This story is a work of fiction. Any appearance of connection to real persons of events is purely coincidental.

My name is Jack Winters. I’m 44 years old and live near Monterey California with my wife and daughter, a senior in high school. We have a son in college.

A couple of months ago, I had an experience which likely changed my life, but I’m not yet sure what it means for me. I’ve never been promiscuous, but I’ve always loved looking at beautiful women. My sex life at home is ok, not fantastic.

I was in Chicago attending a trade show. I’m not in sales, but the show affords me the opportunity to meet with consulting clients for a couple of days. I attended the opening reception at the convention hotel with plans to have dinner with clients.

I soon noticed a very attractive couple in a group. The woman was a stunning red head, at least 5 foot 8 or 9, wearing a tight fitting peacock dress slit up the side almost to her hip. I didn’t think she could be much older than early thirties. The guy was also good looking, taller than she, slender build, but fit based on his well tailored Italian suit. Her low cut neckline revealed an ample bust, but you could tell her boobs were firm but looked natural. I suspect that was the reason several men were giving them rapt attention.

I left the reception to meet my clients at a famous steak house. Dinner was great as expected, but my clients were an older couple who didn’t want to stay out too late. I was back at the hotel a little after 9 pm, too early to go up to my room. I decided to go to the bar for a nightcap.

When I walked in the first thing I noticed was the attractive couple sitting at the bar with only one empty stool next to her! I walked up and said,”Is anyone sitting here?” The red head looked at me with liquid blue-green eyes the same color as her dress and smiled, “No, please take it.”

I was momentarily stunned at her beauty but finally stammered, “Thank you.” The bartender came up and asked what I’d like. I asked,”Do you have any Isley single malts?” He said, “We have Laphroig and Lagavulin.” I said, “Great, I’ll have a Lagavulin straight up with a water on the side.”

When he brought my drink, the guy with the beautiful red head lifted his similar glass to me and said, “Good choice Mate!” I said, “Yes, it’s perfect on a cool night, in a nice place next to beautiful people,” and saluted him back. He said, “Have you been to Scotland?” I replied, “Yes, a few years ago I toured a number of distilleries. That’s where I first tasted the Isley scotches. They’re my favorite. I love the peaty nose.”

He said, “We did the same. My name is Bryan and this is my wife Kimberly. She’s of Scottish decent.”

I said,”I might have guessed! And a bonny lass she be indeed! (attempting a Scottish brogue). Did you kidnap her from the Highlands? And my name is Jack.”

Kimberly looked at me and said, “No, I’m from Dallas, but my grandmother was from Edinburgh. Where do you come from?”

“I grew up in Texas but now I live down near Monterey California.” We continued to chat and seemed to hit it off. Kimberly had about a 3 carat diamond solitaire in her wedding set. From that and how they were dressed, I presumed they were comfortably well off.

Kimberly asked if I was married and I said I was but my wife didn’t like business conferences. She said she didn’t like them much either, but liked to travel. I surprised myself when I said, “I suspect Bryan doesn’t let you get out of his sight!” He laughed. It was like I was flirting with her, but with her husband’s permission.

Every time she turned towards me her knee touched mine, which I couldn’t tell was intentional or not. I caught a glimpse of thigh encased in a black stocking through the slit in her dress. My eyes seemed magnetically drawn to the cleavage down her low cut dress, but I was careful about staring. And, when she did look at me to say something, her eyes drank me in.

I began to feel I was intruding, so I finished my drink and said, “I should let you two get on with your evening,” and made to leave. Bryan said,”We enjoy visiting with you. Look, I have a suite upstairs with a well stocked bar. Why don’t you come up with us for another drink before you turn in?” Kimberly said, “Yes please, you shouldn’t be alone. You’re a fellow Texan!”

Reluctantly I agreed. When I got to their suite, quite a large one, Bryan took off his jacket and loosened his tie. He fixed me a drink and said for me to get comfortable. I did the same and sat in an easy chair. Kimberly took off her heals and sat sideways on a couch next to Bryan and put her feet in his lap. He began to massage her feet and her slit dress was open all the way to her hip. I couldn’t help but look at the top of her nylons fastened by a black garter belt and a very thin strip of her sheer black panties.

Bryan noticed my starring and said, “Kim’s got great legs, don’t you think?” I again couldn’t believe when I said, “I think Kim has great everything!” Kim had been sort of moving her feet around in Bryan’s lap and she said,”I think something’s going on under my feet.”

I started to get up to leave when Bryan said “Kim, I think Jack is lonely. Why don’t you give him a hug.” With that, she got up and came and sat down in my lap and put her arms around me. Her ample breasts were right in my face. The hug forced my cheek right between them. So soft!

Then she leaned down and gave me a long kiss on the mouth. I felt her tongue slip past my lips as she explored my mouth. Kim started moving her hips and I couldn’t help my growing erection. Then she said, “Bryan, now I think there’s something going on under my butt!”

Bryan just laughed, and I said I thought I better leave before I embarrassed myself. Bryan said, “Kim, you gave Jack a peak up your dress. Why don’t you show him what you’re wearing under it?” Still in my lap, Kim turned and lifted her beautiful hair from the back of her neck and asked me to unzip her dress.

With shaking hands, I unfastened the hasp and pulled her zipper down to her lower back. I saw her black strapless bra. Kim stood up and faced me instead of Bryan and slowly let the peacock dress slip downward, exposing her luscious breasts, seeming to overflow the top of her low cut bra. I saw the top of both areolae, a lovely pink on her white flesh.

When the dress was around her hips, Kim leaned forward a little so her breasts were just a few inches from my face. Then she dropped the dress to the floor and my cock jumped in my pants when I saw the black garter belt and tiny bikini panties, barely covering her pubic mound. My eyes were riveted on her mound as she moved her feet apart about a foot. When I finally looked up, Kim had a little smirk on her face as see saw my wide eyes and open mouth.

Bryan said, “How’s the view Jack? It ain’t bad from here either. Kim, turn around and show Jack that glorious ass of yours.” Kim slowly turned and showed she was wearing a black thong over the garter belt. Just a thin strip of black lace down from the waistband completely disappeared between her perfect white cheeks and even in her labia. She wiggled her butt a little for me and then giggled.

I knew I needed to get out of there but was afraid my rock hard dick would give me away. I thought maybe I could hide it under my suit jacket when I stood up. As I started to get up, Bryan said, “I have an idea. There’s a nice hot tub on the balcony. Let’s go for a soak and have another drink.”

I said, “Bryan, I need to go. Besides, I don’t have a bathing suit.”

Bryan said, “Aw, we don’t ever wear bathing suits in a spa. Answer me this, Jack, don’t you want to see Kim totally naked?” I said, “Of course I would! I think Kim is the most beautiful woman I’ve ever seen. But she’s your wife and it’s not my right to see her!”

Bryan said, “Actually, Kim is a bit of an exhibitionist, and it sort of gives me a little thrill to see other men ogle at her. Come on let’s strip and get in the tub. Kim, you go first.”

Kim was still standing with her back to me. She said, “Jack, would you unfasten my bra?”

When I did, she turned to face me and slowly let the bra slip down past her nipples, which already looked to be a half inch long. She put the bra on my head like ear muffs and laughed out loud. Her titties had a natural young girl lift, her nipples pointing up slightly. The areolae were not large and baby pink. I wanted so bad to put my mouth on them and suck.

Next she put one stocking foot in my chair, toes up between my legs and unclipped her nylon from the garter belt. She pushed down the nylon until the top was just below her knee and said, “Jack, you can take it the rest of the way.”

I reached out and slowly rolled it down to her ankle. Her leg was silky smooth. She lifted her foot so I could take it off her heel and then lightly let it come to rest right on my bulging prick. With the ball of her foot, she moved around, seemingly taking the measure of it.

Then she changed legs and did the same thing with the other. She pulled the garter belt around to the front and unfastened it. She put this one around my shoulders and giggled again. Now Kim was standing in nothing but her little sheer thong panties. I could see she had pubic hair through the sheer material. A few hairs were visible around the little triangle of lace.

As I gaped at her pussy, I thought, “Oh my God, dare I hope……” When she hooked her fingers in the waist band and started pulling her panties down, I could see. “Oh sweet Jesus, her muff is exactly the same red color as her hair.” She turned around again with her ass almost in my face, the thong sunk in her crack. She bent over a little closer and to my joy and amazement, slowly pulled them down, giving me a close up view of her glorious pussy. I saw a few more auburn hairs around her slit and up between her cheeks. It was all I could do not to grab her and bury my face in that fabulous ass!

I was so mesmerized by Kim’s glorious body, I hadn’t noticed Bryan had already stripped down to his underwear – small black briefs that clearly showed his erection flattened against his stomach. He said, “Jack, it’s your time to strip.”

“I can’t stand up right now, for obvious reasons!” I croaked.

He said, “I’d be highly disappointed if you weren’t wearing a hard on after seeing Kim nude. See, I am too!” As he pealed down his briefs, his dick stood straight out. I hadn’t ever seen a man with a full erection before except in pictures, and I was surprised how highly erotic he looked. He wasn’t massive, but maybe 7 or 8 inches long, but I was envious of it’s upward curve and uniform color. The thought came to my mind the head of his cock was the same pink as Kim’s nipples.

Kim said, “Come on Jack. You got to see us. It’s only fair for us to see you. Be a good sport!”

I’ve never thought I was particularly well endowed, but what I have I’m proud to have. And at the moment I couldn’t remember when my dick felt bigger or harder. So I thought, “What the hell. I’ll never see these people again and they don’t know anything about me.” I was self conscious, but I stripped. When I looked down at myself, I knew I’m not normally this thick when erect, and I had the sensation of straining to grow more.

Bryan said,”Bravo Jack. I see we do have your full attention!”

Kim looked at my erection and asked,”Did little ol’ me do that to you? Ha!”

Kim brought a bunch of towels to the balcony, which wasn’t visible from other rooms, but had a beautiful view of Chicago’s yacht basin. Bryan opened a bottle of champagne and poured us glasses. It was plenty chilly out, but the water felt great. As I sat there, I thought,’How the hell this this happen? Am I being set up for blackmail or something?’

Kim was all over Bryan, kissing and rubbing her tits in his face. He was eagerly sucking one, then the other. Just as I was thinking I’d really made a bad decision, she came over to me and put her tit on my lips. I was powerless to do anything but lick and suck. Her nipples now looked an inch long. As I was doing that, I felt her hand reach down to explore my dick and balls. She lightly squeezed my balls and then my dick.

Then she was gone back to Bryan. My dick throbbed and while the bubbles hid exactly what we were doing, I slowly started jacking myself. Kim whispered something to Bryan and he laughed. He said, “Kim thinks you’re jacking off. No jacking off in the tub. If you’re gonna jack off, you have to let us watch!” I said nothing.

Soon the champagne was gone and they started to get out and towel off. I couldn’t believe I was still hard after all this time, probably a record. My balls were starting to ache. We went inside with our towels wrapped around. They led me to the bedroom. Kim dropped her towel and lay down on her back on the king sized bed. She pulled one knee back and swung it back and forth, giving me a view of her red pubic hair and slit. I almost creamed at the sight.

Bryan said, “Have you ever seen a woman masturbate?”

I said,”No, not really (I’d tried unsuccessfully for years to get my wife to touch herself for me).” Kim opened her legs and started rubbing up and down her slit. Soon I could see her pink inner labia poking out and it looked slick with her juice. The lips were flared and her pussy looked like a beautiful pink tulip.

Bryan sat in a chair. Kim said,”Jack, I want you to stroke your cock for me.” I looked at Bryan and he said, “Do it for her! It makes her hot to see a man jack off!” I slowly started jacking while I watched Kim’s fingers dance in and out of her pussy and swirl around her clit, which was surprisingly large and looked very firm.

I worried I might cum at any moment and didn’t want to yet, so beautiful was Kim as she spread open her legs. Then she said, “Come closer.” When I came up to her side of the bed, Kim reached out and took my dick in her hand, feeling it up and down. Her fingers were slick with her own juice as she rubbed around the head. Then she said,”I want you to suck my pussy, Jack. Now!”

I’m not believing this. Again I looked at Bryan and he nodded. “Is he gonna knock me in the head if I go down on her?” But my brain was now in the head of my cock. I got on my knees on the bed between Kim’s legs and feasted my eyes on her glistening pussy. I gently opened her lips with my thumbs and breathed in her faintly musky woman smell mixed with her perfume.

I licked up and down and then lightly sucked on her clit. It was as firm as a tiny penis. I loved the feel of her soft fur on my lip and nose. All this time Kim was making little mewing sounds in the back of her throat. Then she shuttered with an orgasm, and I thought she was finished.

But to my surprise, she pulled both knees all the way to her chest. I took it we weren’t through and I started licking again and before I thought about it I was licking her little pink rosebud ass hole. She really liked that, so I pushed my tongue in and out again and again.

I moved my mouth back up to her cunt and slipped my finger in her ass, slick from my tongue. Soon she was writhing her hips in pleasure.

I couldn’t stand it any longer so while still on my knees I reached down and started rubbing my cock again. I felt a hand on my lower back and heard Bryan say, “Just keep working on Kim’s ass, I’ll take care of you.” Then I felt Bryan’s hand removing mine and grasping my dick.

I froze. I had never had a man touch me before. I started to object, but then Bryan started swirling his fingers around the head – his hand was very slippery – obviously he’d put some kind of lotion on it. Then he slowly started jacking me, his hand sliding the full length. I was so near coming I just let him do it. Bryan’s other hand reached between my legs and fondled my balls – rolling and softly squeezing.

As he continued stroking, the other hand moved up putting pressure on my perineum. I could feel a tingle all over down there. Then a finger glided over my anus. Again I froze. I felt the tip of his finger slip into my ass. The nerves in my sphincter clamped down as he wiggled his finger and slipped it in and out. The sensation was indescribable – the burning in the head of my dick and the contractions of my sphincter around his finger.

Just as I was about to blow, Kim put both hands on my head and said,”Get up behind me,” as she rolled on her side. Bryan pulled his hands away. I thought,”Oh shit! I’m gonna cum!” But somehow I didn’t as the feeling backed off just a bit.

I crawled up behind her with my dick right between her butt cheeks. Kim pulled my arm over her and put my fingers on her nipple. She moaned as I lightly tweaked it. She began moving her ass up and down on me. I couldn’t believe she wanted me to fuck her ass. I’ve never gotten to do that but have long lusted for the chance.

Just then Bryan reached in between us a rubbed some kind of lube on Kim’s ass and my dick. With my hand I positioned my dick head against her hole and slowly pushed. Kim gasped but didn’t pull away. In fact, she pushed back against me. Then her sphincter gave way and the head of my dick was inside! I lay there very still for her to relax further.

Then Bryan’s hand was on my ass again as he toyed with my butt hole. I felt his finger go into my ass and rub around. The sensation was electrifying. I pushed back on his finger, wanting him to probe deeper when Kim started pushing down on me again. I slipped further into her. Again she was moaning. I couldn’t figure what felt better, Kim’s ass squeezing my dick or Bryan fingering my ass. But now I just had to start fucking that wonderful ass.

The tingling was starting again and I felt new pressure on my sphincter. I thought it must be two fingers. Then I dawned on me, Bryan had his dick on my ass hole. He pushed and was in. He pulled back and pushed back harder. My sperm was boiling inside me. Kim pushing back and forth.

Kim opened her legs and started furiously rubbing her clit, which triggered a massive orgasm. Contraction after contraction. That’s when Bryan’s dick hit my prostate. I exploded! Never in my life have I shot so much cum. Spasm after spasm, Kim’s contractions milking ever last drop of cum from my balls.

Then Bryan groaned and shot hot cum up my ass. It was hot. I’d never felt my rectum so full and my balls so empty! The three of us collapsed holding each other and laying very still. But my dick was still twitching in her and so was his in me. I would have been happy to spend the next year of my life with my prick up her ass. Amazingly after such a massive ejaculation, my dick was still rock hard.

As spent as I was, I had the intoxicatingly smell of Kim’s hair next to my cheek. I just had to brush my hand over her heaving breast. Damned if her nipple didn’t harden when I touched it.

Bryan withdrew and rolled on his back, a long sigh escaping his lips. I gave Kim a couple more slow thrusts, and reluctantly let my dick slowly slip out of her. I was feeling very affectionate towards them both, but then reality set in. I clapped Bryan on the shoulder and kissed Kim on the cheek and said goodnight as I left their bedroom.

Back in my room, it all seemed like a dream. That’s when the enormity of what had just happened hit me. I’d never had anal sex before, although I’ve always wanted to. I’d never had a man touch me before, much less fuck my ass. I thought, “Am I gay? Am I bi? Will I ever be satisfied with so called ‘normal’ sex again?”

Eventually I fell asleep. I had this vivid dream. Kim was on her knees, still wearing nylons and the garter belt, but no panties. I was up over her, pushing my prick in and out of her ass. I could feel I was about to cum in her. Suddenly, she turned her head around to look at me. But it wasn’t Kim’s face I saw. It was Bryan’s!