It was early Sunday morning, and once again I found myself at the airport, catching a flight to the next city on my work schedule. I spent three weeks of every month on the road, a week each in three different cities. Usually by the end of the first month in a new location, I had found a sexual partner to play with: a couple, a woman, or a man. I’m not exactly straight. I bend in multitasking ways, and you might say I’m bisexual, though I lean toward sex with men more frequently.
This was my third trip to the same midwestern city. The first month, I had hooked up with a woman; the second month, with a man. The woman turned out to be a one-time thing. Although we enjoyed ourselves, she was married and only wanted a single fling. The man, also married, was looking for a repeat fuck buddy, and we had already planned to meet again on my return.
The plane was packed, as usual for these direct flights. I had a window seat a few rows behind first class, and thanks to priority boarding, I was already settled when the next group boarded. An older man with gray hair and a cane took the aisle seat. Toward the end of boarding, a woman claimed the middle seat beside me.
I’m not much of a talker on flights, so I gave her a brief nod and returned to my book. Shortly after takeoff, once the seatbelt sign went off, I was gazing out the window when she tapped my arm. She asked what I was looking at and explained that this was her first flight in many years. She didn’t understand the entertainment screen in front of her and wondered if I could help. She was very pleasant. Her name was Terri; I introduced myself as Dick, which earned a raised eyebrow. She was quite chatty, asking questions and gradually drawing me into conversation.
Terri was attractive, about my height at 5’6”, with shoulder-length dark hair and a nice figure. From what I could tell as she settled in, she had sharp features that gave her a slightly masculine edge. As we talked, I learned we were staying at the same hotel. She lived only about ten miles from my home. A sales representative for a tech company, she rarely traveled out of state. The more we spoke, the more interested I became. She wasn’t married and had no long-term partner, male or female.
After we landed, we walked together to baggage claim. When I asked how she planned to get to the hotel, she said by taxi. I offered that if she waited, I was picking up a rental car and she could ride with me. After checking in, we discovered we were on the same floor, her room directly across from mine. She asked if I had dinner plans. I told her no, but a friend was coming by around 9 p.m. We ended up eating at the Chili’s next door, chatting through the meal and getting to know each other better: hobbies, likes, even sexuality. I was honest and told her I enjoyed both men and women. Terri preferred men only, though she gave me an inquisitive look when I mentioned both.
Around 8:00, we returned to the hotel. I needed to get ready for Bob.
Bob arrived just after 9:00. I had just showered, clean inside and out, and was still in my bathrobe when he knocked. I opened the door; he stepped inside, wrapped me in a bear hug, ground his hardening cock against me, and planted a sloppy kiss on my lips. Unbeknownst to me, Terri had watched through her peephole before the door closed.
We settled on the couch with beers, making out like teenagers. I rubbed his big cock through his pants; it snaked halfway down his leg. I was horny as hell and could barely wait to taste that thick shaft, lick and suck it until he was ready to fuck me. His tongue was deep in my mouth, exactly where I wanted his cock. Finally I freed his zipper and wrapped both hands around him. At a full seven inches and impressively thick, my fingers barely met. He pushed me down; I engulfed him, caressing his balls, licking the head, doing everything I could to make him feel good.
My own cock went from semi-hard to rock-solid the moment he entered my mouth. Bob pulled me off and said it was time to get more comfortable. I shrugged off the robe and helped him undress. We fell into bed with him on top, fully dominant now, grinding his thick shaft against me while kissing and whispering how he’d been looking forward to this for weeks, how he couldn’t wait to be inside me, how he’d been dreaming of fucking me.
He flipped me over and dove in, eating my ass like a starving man, tongue and fingers spreading me open, getting me ready. He reached for the lube, slicked my hole generously, then coated his cock. He lined up and pressed in. I pushed back to help; the initial breach burned deliciously, the stretch stealing my breath. He pulled out and pushed in again, repeating until he was fully seated.
I felt completely full; my cock had shrunk to almost nothing. When he started pumping, rubbing my prostate with every stroke, the pleasure built quickly. Bob grunted, kissed the back of my neck, and thrust faster. After about ten minutes, he stiffened, moaned louder, and with a final bellow, came deep inside me. He collapsed briefly, whispered how awesome a fuck I was, then rolled me over and attacked my cock, sucking furiously until I exploded in his mouth. We finished with a messy snowball kiss.
Afterward, as we lay chatting, I asked if he could visit again before I flew out at week’s end. He said no; too much was going on, and his wife had plans he couldn’t escape. I teased him about bringing her into our arrangement someday. He laughed it off at first, insisting she would never participate. I suggested dinner at a nice restaurant next month instead. He said he’d mention it and see. When I explained why, I simply said I wanted to meet the woman who got fucked by that sausage-sized cock. We both laughed.
The next morning at breakfast, I saw Terri sitting alone. After grabbing eggs, sausage, juice, and a roll, I joined her. The conversation opened with her asking how my evening with “my friend” had gone. She had stayed up late and heard him leave after 1 a.m. She hoped we had “caught up.” The piercing look she gave me told me she knew exactly what kind of friend Bob was. I acknowledged we had had a good time, then steered the topic to dinner after work. We agreed on 7 p.m.; she would pick the restaurant.
My workday ran long, so I didn’t get back to the hotel until 6:45. I needed to shower and change. A knock came at the door; it was Terri. She looked stunning in a tight pantsuit that showed just a hint of cleavage. The pants hugged her ass perfectly. In the front, I thought I glimpsed a bulge, but I dismissed it as poor lighting. The restaurant was cozy and intimate, not far from the hotel, so we walked. Three scotches each, one before dinner, two after—fueled the conversation, which gradually dropped to a near-whisper.
Terri asked about Bob and what we had done during his visit. She finally admitted she had seen our intimate greeting through the open door and heard the sounds coming from my room late into the night. Those sounds had turned her on. I suggested we continue the discussion in private. I paid the bill, and we walked back to the hotel. In the elevator, she kissed me, not a polite thank-you but a full, passionate, tongue-deep kiss.
When we reached our rooms, Terri asked if we could keep talking about Bob. She opened her door and pulled me inside. Her room mirrored mine. I sat on the couch while she poured us drinks. She said she would be back in a minute and disappeared into the bedroom. Moments later, she returned in a semi-transparent black silk nightgown. I could see her breasts clearly through the fabric and made out a thong underneath. She looked incredibly sexy. Sitting beside me, she said, “Dick, now please tell me about you and Bob.”
I told her everything: how we had met last month, how we had planned this visit, that he was married, and how we had had sex both times. She pressed for details, oral or anal, how big he was. I decided to hold nothing back. The confession turned me on, and I could see the sparkle in her eyes as I described how his thick cock stretched me at first, how he was a dominant top and I gladly bottomed, how we had fucked twice the night before, and how we had joked about dinner with his wife next time.
Throughout my story, my cock had hardened and bulged noticeably down my pant leg. Terri noticed, reached over, and lightly placed her hand on it. Looking me in the eyes, she asked if I was ready for a surprise.
By then, I was certain she wanted sex, but her surprise still caught me off guard, and I welcomed it. Terri stood, then straddled my lap, pulling up her nightgown as she did. I felt a bulge against my groin. She leaned in, kissed me aggressively, then pulled back and whispered, “Dick, would you suck my cock?” She stood, pulled me to my feet, and led me to the bedroom.
She undressed me down to my boxers, pushed me onto the bed, then lifted her nightgown off. Her breasts were gorgeous, C-cups with pink nipples and small areolas. Her cock remained tucked between her legs beneath the thong. She straddled my chest, her groin inches from my face. Rising slightly, she reached down, pulled out a sweet cock, not fully hard yet, but growing. Her eyes locked on mine as she rubbed the head across my lips and pushed inside.
It had a slight musky, salty taste at first, but then it swelled, longer and thicker. I wrapped my hand around the shaft. Even with most of it in my mouth, three or four inches remained outside. I rolled her onto her back and worshipped her cock: kissing the head, licking the shaft, cradling her small balls. She was a grower, probably two inches longer than mine, nicely curved upward, pink, and delicious. Her pre-cum leaked salty and enticing. I loved her surprise.
We moved into a 69 with her on top, both sucking eagerly. She played with my balls, taking them one at a time into her mouth for a tongue bath, while her finger circled my hole lightly, tapping the rim. Following her lead, I pulled her down and ate her ass hungrily. Feeling my own orgasm building, I rolled us over, pulled out, turned us face-to-face, and we kissed deeply, grinding together as the heat rose.
Terri whispered, “I want to fuck you first.” She positioned me on hands and knees, licked and ate my ass with sexy moans, praising my gorgeous ass and pretty pink rosebud. She grabbed the lube from the night before, slicked my opening and her cock, then asked if I was ready, lover.
She lined up and pushed in steadily until all eight inches were buried. She held still for a moment to let me adjust. My cock softened on entry but leaked pre-cum steadily. Terri pressed us flat; her breasts felt wonderful against my back, her hair tickling my shoulders. She kissed my neck and ears while pumping steadily, gradually increasing speed and force. Breathing harder, she pounded deep. With a groan, she stiffened, flexed inside me, and came. Still buried, she whispered how wonderful it had been.
Her cock softened and slipped out. She rolled off; I turned to her, and we embraced and kissed passionately. We lay talking and cuddling for about an hour. It was getting late, I had an early presentation the next day, so I suggested we sleep. She pointed out I hadn’t come yet and offered to suck me off. I couldn’t refuse. Her mouth felt like velvet; I lasted less than five minutes before erupting down her throat. She swallowed everything, kissed me good night, and we cuddled until we fell asleep.
The next evening, after a long workday, we met at the same restaurant. Dinner was delicious but hurried; we both wanted to get back to the hotel. That night, Terri came to my room in a bathrobe over a red, transparent negligee that left nothing to the imagination. Her nipples were hard; her cock tented the panties beneath.
Our embrace was passionate and urgent. Tonight, she wanted my cock inside her; she wanted to be treated like the beautiful woman she was. Clothes hit the floor quickly. Her mouth devoured me, taking me deep while caressing my sack and bringing me right to the edge. I pulled back, kissed her (tasting myself on her tongue), and lubed her opening generously, then coated my own hard cock.
Terri asked me to go slow; it had been a while since she had had a man inside her, and never one as thick as me. I pressed the head against her opening. She pushed out; I slipped in just the head and paused. She pulled me deeper. I stopped again to let her adjust. Opening her eyes, she said, “Please, Dick, take me.”
I buried myself fully—six or seven inches deep. She groaned but kept her eyes on mine. I moved slowly at first, pulling almost out before plunging back in. The look on her face, pleasure mixed with a touch of pain, was adorable. We fucked for fifteen or twenty minutes, time melting into pure intoxication. Her cock stayed hard, so I stroked it lightly. As my own orgasm neared, I whispered, “Come with me, babe.” Those words pushed her over; she clenched around me. I erupted in powerful spasms; Terri unleashed a torrent of cum like a fire hose.
I collapsed onto her chest, still buried deep, our cum spreading between us like glue. We kissed passionately, breathing hard. As I softened and slipped out, a stream of cum followed. Terri rolled onto her side; I spooned behind her. Within moments, she was asleep, breathing softly.
Morning came quickly. I had one more workday; Terri was flying home. After we showered, she begged to suck me again. I couldn’t refuse that sweet mouth. After she swallowed everything I had, we dressed, she returning to her room, I heading to work. Text messages flew back and forth, some sexy, some sweet. We made plans to meet on Saturday afternoon back home. We both wanted to keep exploring this new connection and see where our feelings and friendship might lead.
Saturday afternoon arrived with a mix of anticipation and nervous energy. We had been texting nonstop since Terri flew home, flirty messages, explicit photos exchanged (hers first: a teasing shot of her cock half-hard in black lace panties, mine in reply: slow strokes while replaying our hotel nights), and careful logistics. We settled on my place at 2 p.m. No dinner, no excuses, just hours to explore without interruptions.
I had the house ready: fresh sheets, lube within reach in every room, chilled wine, and soft lighting. The doorbell rang and my pulse jumped. There she was in weekend-casual perfection, fitted jeans hugging her hips and ass, a soft V-neck sweater hinting at her breasts, dark hair loose, just enough makeup to sharpen those striking features. She carried a small overnight bag and a wicked smile.
The door had barely clicked shut before she was on me, fingers in my hair, mouth claiming mine in a deep, hungry kiss. Our bodies pressed together; I felt her cock already thickening against my thigh. We stumbled toward the bedroom, shedding clothes along the way. By the time we reached the bed, we were naked and laughing breathlessly.
We tumbled onto the sheets. Without a word, Terri spun around and straddled my face, lowering herself until her thickening cock brushed my lips while she leaned forward and swallowed me to the root in one smooth, wet motion. The 69 hit us like wildfire, slow and sensual at first, then building into something raw and perfectly mirrored.
Her cock tasted intoxicating: warm skin, that familiar light musk from the drive over, and the first sweet beads of pre-cum coating my tongue as she hardened fully against me. I licked slowly from base to tip, tracing the upward curve, then swirled around the head before taking her deeper. I relaxed my throat and worked more of her eight inches inside, my nose pressing into her smooth groin. Terri moaned around my own cock, the vibration traveling straight to my balls and making me throb harder in her mouth.
Her technique was pure perfection: tight, rhythmic suction that pulled me in, her tongue flicking relentlessly along the underside, one hand gently rolling my balls while the fingers of the other teased my taint and then circled my hole. She eased one slick fingertip inside me, then a second, scissoring softly and brushing my prostate with every slow thrust of her hips. I matched her exactly, sucking her with the same hungry rhythm, my hands spreading her firm cheeks wide so I could bury my tongue between them. Her rosebud was hot and silky; I licked broad circles around it, then pushed my tongue inside, tasting her deeply as she ground back against my face with a muffled cry.
The room filled with wet, obscene sounds, slurping, moaning, the slick slide of mouths on cocks. Pre-cum flowed freely from both of us now, mixing with spit that dripped down my chin and her thighs. We edged each other mercilessly: whenever one of us sped up and felt the other’s cock start to pulse, we would pull off just enough to whisper “not yet” before diving back in. Her fingers worked deeper inside me, curling perfectly against my prostate until my legs trembled. I answered by sucking her harder, hollowing my cheeks, one hand stroking what I couldn’t fit in my mouth while the other fingered her in return.
We stayed locked like that for long, delirious minutes, bodies rocking together, sweat building, breaths coming in desperate gasps around each other’s cocks. The pleasure coiled tighter and tighter until neither of us could hold back any longer. Terri lifted off first, turning to kiss me fiercely, our combined tastes, salty, musky, sweet—mingling on our tongues in a messy, passionate exchange.
“I need you inside me first,” she whispered, voice husky. She grabbed the lube, slicked me, and sank down onto my cock in one long, shuddering motion, riding me with slow circles that quickly turned into deep, bouncing strokes. Her breasts swayed under the remnants of her bra; her own cock leaked steadily onto my stomach as I thrust up to meet her. We flipped to missionary, our favorite, her legs over my shoulders, eyes locked as I drove into her. I stroked her cock in time with my thrusts until we both came hard, her release painting our chests while I filled her deep.
We collapsed in a sticky, satisfied tangle, kissing lazily as our breathing slowed. After a few minutes, Terri traced lazy circles on my chest and grinned. “I brought toys… and I want to play dress-up with you.”
She slipped into the bathroom with her bag. When she returned, my mouth went dry. She wore the red transparent negligee from our hotel night, but now the harness was buckled over it. The realistic silicone cock, thick, veined, and exactly my size, jutted proudly from her groin. Her own real cock remained free beneath it, hard and curving upward, creating a breathtaking double-cock sight. She had freshened her lipstick to a deep red and added smoky eyeliner, looking every inch the powerful, seductive woman with a delicious secret.
“New game tonight, lover,” she purred, voice dropping into a low, commanding tone. “I’m Mistress Terri, your dominant boss, who just found out her favorite employee has been sneaking around with a married man named Bob. You’ve been a very bad boy, and now you’re going to make it up to me however I want. And trust me… I want it all.”
The role-play hit like gasoline on fire. She climbed onto the bed, both cocks bobbing, and pointed at the floor. “On your knees, employee. Show your boss how sorry you are.”
I knelt immediately. She fed me her real cock first, deep, slow thrusts into my throat while I stroked the silicone one. “That’s it… suck the cock your boss has been hiding from everyone while you were busy with Bob,” she teased, voice dripping with mock disapproval. “Now the strap-on. Get it nice and wet for the punishment you’re about to take.”
After I had worshipped both, she had me on all fours at the edge of the bed. She lubed the silicone cock generously and pressed the head against my hole. “Take it, slut. This is what happens when you cheat on the company.” She pushed in slowly but steadily, the firm silicone stretching me wide in a different, relentless way than flesh. When she bottomed out, her real cock hung heavy between my legs, brushing my balls with every thrust. She started fucking me with long, powerful strokes, pulling almost out, then driving deep, while her hand reached around to stroke her own leaking cock against my taint.
The dual sensation was mind-melting. She slapped my ass lightly, kept the dirty talk flowing: “Feel how deep your boss is? Bet Bob never fucked you like this. You’re mine now.” I was moaning, pushing back, completely lost in the game. She reached around and stroked me in time with her thrusts until I was right on the edge.
She pulled out, flipped me onto my back, and straddled me again, this time lowering herself onto my real cock while still wearing the harness. The silicone cock rested hot and heavy on my stomach as she rode me. “Now fuck your boss while she wears her toy,” she commanded, eyes gleaming. “Make me come while my big cock watches.” I thrust up hard, gripping her hips; she stroked the strap-on like it was real, talking filth the whole time until we both shattered again, her real cock erupting across my chest, mine pulsing deep inside her.
We weren’t done. She grabbed the double-ended dildo from her bag, slicked both ends, and we knelt face-to-face on the bed. “One more round, employee,” she whispered, still half in character but softer now. “Let’s both get fucked like the dirty little secrets we are.” We each took an end, rocking together slowly at first—kissing deeply, staring into each other’s eyes as the toy slid in and out of us in perfect sync. The shared rhythm, the way we could feel every movement through the flexible silicone, built into something almost hypnotic. We came one last time, her stroking us both, me whispering her real name as we shuddered together.
By evening we were spent, showered together with slow, soapy touches, then ordered takeout and ate naked on the couch, talking softly about feelings, boundaries, and how natural this all felt. When she left late that night, she kissed me at the door and murmured, “Best Saturday I’ve had in years, Dick. Next weekend… maybe we invite a little more role-play. Or maybe we finally meet Bob’s wife for that dinner.”
I couldn’t wait to find out which.
