Two Of The Seven Watching My Wife

This story is about two if the seven deadly sins, how it lead (almost) to the ruination of a young man, and his marriage. It contains wife swapping, cross dressing, and both straight and gay sex. Enjoy!

The worst part was how stupid I felt. No one likes to admit they were played. I thought I was smarter than that.

Stephanie was a sporty, spicy redhead beauty, about 5'4", just a magnificent body and amazing gravity defying tits. She was intelligent, charming, men fell in love with her at first sight. I was a little taller, 5'8", short cropped blond hair buzzed on the sides, very sporty, even competed in MMA a few times. Lean, even lanky, fit, tanned and focused.

Steph and I met at Freshman orientation, college Day 1, (I swear). We were fast friends, then dating then married right after graduation. I started a firm my senior year, and by the time we left the dorms we had a good income, a growing business, and the world at our feet.

The funny thing about finding success early, is it makes you feel invincible. We soon had enough income coming in that we traveled, and of course tried everything we could, from skydiving to a sex club in Vegas. The sex club thing was pointless; we were the best looking couple there, but just before we left an older, but fit couple took us aside, we did some soft swapping, a little oral experimenting, then fucking in the same room with our wives. In truth, it felt liberating to watch and be watched, but it was hardly and experience either of us wanted to pursue.

But that experience lead to my fall. Greed. Lust. Of the Seven deadly sins, I fell for two of them at once.

My business was attracting attention, I was approached to sell out a few times, but it was growing and I had no thought to hand it over to anyone else. Until I met Bart.

Bart was an attorney for a large conglomerate in Big City. He contacted me and suggested we meet at lunch to discuss my "future". We met at a local racetrack, and I really enjoyed his conversation, he was older, maybe mid 40s, and really knew the business, kept telling me how impressive my accomplishments were. He really fed my ego, that should have been my first red flag. Then, he announced he'd rented us each a car, and in no time we were racing down the track in hot Italian sports cars! I had the time of my life, and after a few laps we relaxed in the driver's lounge with scotch and cigars. I left feeling like a million bucks. At last I'd arrived in the winner's circle. I really liked Bart, I thought his friendship was real.

When Bart called a few days later, offering to host my wife and I for a weekend in wine country, I leapt at the opportunity to show off to Stephanie, and let her meet Bart.

Even after the track day, I was not prepared for what Bart hard in store.

A limo picked us up, we flew to a private chateau in northern California, on arrival the entire staff greeted us by name, treated us like royalty, it was the most amazing weekend of our lives. I wanted more.

We also were introduced to Bart's wife, Una. She was half his age, if that, a smoking hot, olive skinned Italian beauty, evidently a model of some fame back home. She had this way of seducing me, without being overt. It was the sexy glances, the way her eyes lingered on my chest, or ass, or legs, the brief smile when she looked my way. She'd whisper "When you enter the room, everyone knows you are an alpha!" or "I love the way you swagger, like a cowboy or a champion!" I was completely taken. Stephanie was not, but I barely noticed her annoyance.

The weekend passed too quickly, so a few days later when Bart called, I was eager to get together again. He'd drawn up a contact to acquire my firm, and added more zero's to the price than I'd ever seen before. My head was spinning already, when I heard Bart say "You know, Una was very taken by you, very interested in you, and of course, Stephanie is a very beautiful woman too. Have you two ever partied with another couple?"

The question completely caught me off guard. My brain slowly switching gears from counting all those zeros, to what he was implying; I nodded, absently. "Yea, a little." I said. "Good!" Bart exclaimed, happily. "Why don't you two come over for dinner tonight, and we can discuss further!"

I rushed home to show Stephanie the contract, and tell her about dinner. The wife-swapping I left out, too distracted about everything, and maybe thinking too much about fucking that totally hot Una. I felt invulnerable, and let my guard down. Luckily, Stephanie immediately sent a copy of the contract to our attorney for review.

Dinner at Bart's massive lake house was amazing, he was a perfect host. Una looked incredible, and despite my best attempts at decorum I caught myself staring at her tits or ass every time she got up, or leaned over. Steph noticed, and of course was annoyed, but otherwise enjoyed our evening.

After dinner, we retired to the deck for brandy and dessert, when Bart asked "Did Cliff discuss our offer with you?" Stephanie started to talk about the contract when Bart interrupted her, "No, I mean the other offer" and visibly undressed her with his eyes, while Una smiled at me with a sultry wink.

Steph grabbed my hand and let me back into the house, saying "We need a moment" over her shoulder.

"What's going on?!" she demanded.

"Bart proposed we do a little wife-swap, that's all." I replied, innocently as I could. "We kind of did it once in Vegas, I didn't think it was a big deal"

"You just want to fuck that Italian whore!" she accused. "She's been flirty with you non-stop!"

"Yes, that's true." I admitted, my ego inflated even more. "No big deal, I mean, Bart's not bad looking..." I tried to argue, knowing that if Steph said no, my fantasy of nailing the sexy Una would evaporate, maybe that contract with that giant payday too. Greed, Lust. I was seduced. We talked a little more, Stephanie was moments away from storming out of the house, when I said "What's the big deal? You suck his cock a little, hold still while he fucks you, and..." My brain was screaming at my mouth to stop, I honestly didn't believe those words came from me.

Stephanie froze, looking at me like I was demented. Her eyes were cold as steel, they locked on mine, her jaw set firmly. Then she surprised me, and took my hand roughly, "Let's get this over with." and we rejoined Bart and Una on the deck.

She dropped my hand like it was a dead fish and took Bart's, Saying "Come on, handsome!" and leading him away. I put my arms around Una and she whispered "This way", leading me to a nearby room. There was a king bed, a giant wooden 4-poster bed frame, towels and massage oils laid out, a bottle of champagne on ice, two glasses. Perfect. I leaned over to kiss her.

That's when it went wrong. She twisted and dodged my lips like it was a joke, giggling and teasing, but I found it obnoxious, having just risked my marriage to even be here. I started to feel her up, she again twisted and giggled like it was some kind of game. This went on for a while, I was getting more and more annoyed, it was the farthest thing from sexy I'd ever imagined. It was like wrestling with an octopus, she kept giggling and saying "Oh, you want this?" while she twisted away. Eventually, I got her panties off and her dress pulled up, forget kissing, or a blowjob, and even though I was hot to eat her pussy, I gave up on that too. She wasn't resisting, as much, just making it hard to do anything. Even pulling at my hands as I tried to put a on a condom, until I pushed her down on the bed, roughly. Once it was on, eventually, then I pinned her down (Which she seemed to like) and roughly drove my cock into her sopping wet cunt with one forceful stroke. Una gasped, bit my ear playfully and said something sexy in Italian, followed by "Yes, my hot young lover! Deeper now!"

By this time, All I wanted to do was cum and get the fuck out, as I railed her, her face changed from an arrogant tease to a desperate, lustful longing, her nails dug into my back and she started to cry out "Oh, yes! Yes! Deeper! Harder, my love! Oh, god, yes! YES!" over and over, her legs spreading wider and her hands on my ass pulling me in deeper. I pumped her harder and harder, glad to at least finally feel that pussy I'd been dreaming about, then she started screaming "Yes! Yes! Oh, fuck me like an animal! You beast! My Bull! Make me your slut! Oh! Yes! Fuck me like a bull! Like a bull!!" Normally, those word would be major turn-on for me, but now the magic was gone; I was like a machine, focused only on my own orgasm.

I lost track of time, until last I felt my climax building. I held her down and viciously drove my cock deeper into her sopping wet pussy, pounding it as hard as I could, anything to finish. Una screamed again, digging her nails in and shuddering uncontrollably. "Oh! My bull, fuck your slut! Fuck me!" she cried out.

I started to climax, but didn't slow down, feeling the hot jets of my cum erupting from my cock over and over again. The condom must have ripped, as I looked down to see my cum squiring out from her pussy with every thrust, and for some reason that only made it hotter, and I kept fucking even as my orgasm subsided.

Eventually, exhausted, I rolled over and lay on my back, noticing for the first time both Bart and Stephanie were at the door, Bart looking angry and Steph annoyed. Bart made a display of impatiently checking his watch, looking over at Una with disgust. I was still catching my breath, when Una climbed to her knees and started to suck my dripping wet cock.

"Oh, my bull! My hot animal lover!" She pleaded with me, eagerly licking the cum and pussy juice off my dick, balls and thighs. Bart marched over and pulled her off, roughly pushing her out of the room, saying "You can find your way out, I'm sure!" he scowled as he stormed off.

Stephanie walked over, handing me my clothes. "We've been watching you for at least 15 minutes, Old Bart barely got his condom on before he started to shoot. A three-pump chump for sure!" She grinned.

"Stephanie, that was the worst sex of my life, a huge mistake. I'm, so sorry." I confessed, honestly ashamed of myself.

"Oh, you will be sorry. Payback is coming!" she warned me. "I let him fuck me, for you. I let you, my husband, fuck a whore. You are in deep, mister!" My face burned red, with the realization of what I'd done. "The next time I fuck a guy that's not my husband, I pick him, not you!" She told me, firmly. "I think I'll take a girls trip to Vegas, and fuck some guy from a bar. A guy I pick, not some pencil-dick creep." I nodded, I deserved this, I felt like a fool. We dressed and left.

To top everything off, our attorney contacted us the next day, warning not to sign the contract. "It's got so many dependent clauses, performance stipulations, and penalties, you'd be lucky to see a dime over the next several months, if not years, it's barely legal, more like a scam." I was crushed, my ego had blinded me, Bart was a total fraud, but felt like at least I dodged that bullet and kept my company.

A few months later, Stephanie surprised me with tickets to Vegas. I was excited, talking about the things I wanted to do, or see, when she stopped me and said, sternly "Oh, no. This is your payback weekend. No questions, no turning back, you owe me. Now, I own you. This weekend, your ass is mine." "I thought you were taking a girlfriend?" I asked, remembering her threat to me. "I am!" she grinned, but refused to discuss it further.

I was taken aback, but still excited. We landed, and checked into a very nice hotel, off the main strip by a ways. Right after we checked in, there was a knock on the door.

"That must be the mani-pedi I ordered." she explained. And let the manicurist into the room with her gear. As the girl was setting up, she turned to me and said "Go shave. Everything. It all goes, from just below your your ears to your toes. Now!" and pushed me into the bathroom. I'd been a swimmer in high school, so this wasn't unusual for me, but an odd request from Stephanie. Remembering her words of warning from earlier, I turned on the shower and closed the door.

About 40 minutes later, completely smooth and clean, wearing only a robe I rejoined Stephanie in the room, only to see her and the manicurist waiting. Steph was wearing a robe, her freshly painted nails drying. She's picked a hot red color for both her hands and feet, and it looked stunning on her. When she saw me, she got up and indicated that I take her place in the chair. I'd never had a manicure before, so I shrugged and sat down. I closed my eyes while Steph and the girl made small talk, she did my fingernails then my toenails, it felt odd but not unpleasant. Then, I smelled wet paint and looked to see her painting my nails the same hot red color as Stephanie had. I looked over at Stephanie in a panic, but an angry glance from her and I fell back into my seat, praying that no one saw me like this. When she finished, she and Steph looked me over like a prized calf, fist-bumped each other and then the manicurist left, giggling. I was humiliated.

Steph announced "Time to get dressed!" and my first thought was to find a way to hide my nails, but she handed me a pair of lacy pink panties. Looking closer, I saw they had a pouch in the front; these were not girls panties.

"Hurry up!" She said, impatiently.

It took me a little bit to figure out how to get them on, then arrange my junk so they fit. Next she handed me a garter and stockings. "Quickly!" she commanded.

She helped me get these on, I had this feeling of dread, nagging at me. Next, came a lacy bra. I looked it over, it had padding in the front like breasts, even nipples. "Where did you get all this?" I asked, incredulously. "Not a word!" she warned. She handed me a dress, and shoes. "What the hell is going on!" I demanded, at last. She scowled at me, but helped me get this dress on, then the shoes (Thank god they were flats, not heels!)

Finally, she applied makeup to my face, eyeliner, lipstick, the whole works, topped off by a wig. Stephanie seemed to have such a good time dressing me, happily humming a song and smiling, I kind of relaxed and went along with her. Finally, she finished, stepped back and smiled. "Go look in the mirror!" she said.

I turned and looked. I didn't recognize myself. A handsome woman stood there, a slutty dress, cut away at the midriff, the sleeves hanging down just enough to cover my muscular arms, I turned and looked from a different angle. She had done an incredible job transforming me, I was shocked.

"Wow" I said, in spite of myself. "You did an amazing job!' She beamed, proud of her work. "Now, can I change and take you to dinner?" I asked.

"Hardly!" she replied. "We're going out for cocktails, just my sorority sister Vicki and I." She explained, taking my arm and posing us in the mirror. She looked delighted. I was horrified. "You can't be serious!" I begged.

"As serious as you were when you asked me fuck your business partner!" She reminded me. I looked in the mirror again. I shook my head, and was about to say something, when Stephanie looked me square in the eye and said "This is my revenge. If you chicken out, you can spend the rest of our marriage sleeping in the guest room. Pull it together! It's just a dress, guys wear'em all the time here!" I took a deep breath and sighed, nodding. She slapped my ass and told me "That's my girl, Vicki! Now, sell it!"

The rest of the evening was a blur, I was terrified someone would call me out, notice I was in drag. At the bar, Steph was noticed immediately by the other patrons, she drank in the attention, flirting and dancing. A couple of black guys in nice suits bought us drinks, sending me into a panic, but Steph thanked them and said we had company coming. (We did?) Twice, two different drunk businessmen would sit next to me and try to start conversation, but I was too scared to even talk, so they seemed to get bored and drifted off. After an hour or so, I began to realize that no one was freaking out when they saw me, and started to relax, even enjoying the occasional whistle or guy checking me out. Steph had left to go to the girls room, I was not ready to try that so I stayed behind. A pair of younger, frat types sat near me and started making suggestive remarks, I suspect they knew I was in drag and did it on a dare, it was still fun to play the role and flirt a little, but after they realized I wasn't cruising for sex, they left. Maybe this wasn't so bad, I thought.

Eventually, I did get up and dance, trying to mimic Stephanie's style, and at least appear female. In fact, I didn't feel feminine, or for a moment considered myself a woman; I felt like I was in costume, a cosplay. I'd read that performers feel different in makeup, and I did: More daring, less inhibited. It did feel liberating a little. As a man, I couldn't check out other men, or women, without appearing to leer or stare, but as a woman I was almost expected to eye-ball all the meat on the dance floor, and shared my opinion with Stephanie "That guy has a nice ass!" "Oh, Vicki!" She giggled and we talked about other hot guys, or slutty girls, laughing and winking at each other. I played my role well, and I guess Stephanie really did go to Vegas with her girl friend. Maybe I could survive this. I relaxed, and even acted a little slutty, showing off for guys who bought me drinks or gave me attention. I flirted, giggled, and kind of enjoyed myself. "Vicki the slut", I thought, laughing at the situation.

On the dance floor, I danced with men and women, not sure who suspected I was in drag, but no one seemed to care too much. I felt hands touching my waist, my tits or ass, dancing as a woman was very different than as a man. Quickly though, I learned to be defensive, to twirl away from aggressive men.

At one point, I lost sight of Steph, and while looking for her I felt a guy push his groin into my ass. I turned to escape, and push him away but he trapped my hand over his crotch and pushed the outline of his semi-hard dick into my palm. Even though his slacks I could feel it's size and weight. He grabbed my arm and pulled me along, saying "This way, baby! I got what you need!" I said "No! My date is..." But he tugged my arm harder. I followed for a moment, just our of curiosity. He was a tall, thin black man, late 20s, well dressed, even though he was at least 6'4", I didn't notice him before.

He roughly led me down where the restrooms were (I had been avoiding them all night, for obvious reasons) but then took a detour out a door and into the dark alley. He spun me to face him, and said "I know you've been hungry for my meat, suck me baby!" as his free hand started to fumble with his belt. "No, I want to get back..." I said, but he started to push my shoulder down.

I grinned at him, then popped him in hard the throat with my free hand, he tried to gasp, instinctively protecting his bruised larynx with both hands, then I leaned over and punched him in the nuts. "I'll tell the bouncer you're out here." I said, and went back into the bar, leaving him writhing on the ground.

I rejoined the crowd on the dace floor, determined to be more careful, but now concerned about Stephanie's whereabouts.

Then, Steph appeared, arm in arm with a stranger. He was tall, wide shoulders, a powerful gait, well-dressed handsome, blonde surfer hair, about 30. "This is my girlfriend, Vicki" Steph said, "Vicki, this is Richard" I froze, but Richard took my hand in his big, meaty paw and gently shook it. "I love that dress! You look so hot!" he said. I think I blushed. Stephanie was hanging off one arm, he offered me his other one. Steph nodded, and the three of us left.

Once we got to our room, Stephanie started kissing him, making a show for me, I guess. I excused myself to use the bathroom (At last!) and pissed in the sink as not to give away my disguise with any man-noises. I washed my hands, checked my look, and started to think of a reason to leave. Steph had told me she was going to fuck a stranger as my punishment for treating her like a whore, and I guess this was it.