Work Flirting To Cuckold Experience

I'd worked with Michelle for around two years. I'd also fancied Michelle for around two years. As first sight, I knew she was someone that I'd really like to be with.

By her own admission, she would never have been a model. She was very pretty but in a plain sort of way. She was forty-one years old, with three teenage children, but nature had been kind to her. Her face showed not much sign of ageing, no blemishes at all. Her face made her look younger than she was, and she was forever getting compliments about her skin looking so good. I was twenty-five years old and single.

Michelle had been married to Neil since they were eighteen. They were the same age, childhood sweethearts, and even though I really fancied her I could see why they'd been together so long. Neil had worked with us for a couple of months when he got made redundant. Michelle worked part-time, so Neil came to work with us to keep some extra income coming in. He left when he was offered a job at one of his former employer's rivals.

He made me feel a little guilty about fancying, and sometimes fantasising, about his wife because he was such a nice guy, easy to get along with and even making and joining in with flirty comments about her. There was no hint of jealousy or anger if anyone made any sexual references to her, providing people didn't go over the top. I'd even joked with him that I'd called her My Chelle one time, making a play on words to her proper name, saying I wanted her for myself, not realising at the time she was married.

Things came to a head after Neil had left. Our shifts didn't always cross, but I needed to speak to her one day to discuss a work issue. As I walked towards where she'd be, she was bending over replacing some price labels. Her arse was quite big but not massive, just enough to put her into PAWG status. Coupled with her 38D tits she was delightfully curvy. I wolf-whistled to myself as I approached her, and she got up and frowned at me.

"Are you checking out my bum again, Danny?" she asked, pretending to tut at me.

"It shouldn't be so damn nice then, it's like an upside-down love heart," I told her.

She blushed. "You shouldn't be looking at married ladies like that, it's very naughty, especially when they're almost old enough to be your mother," she playfully scolded me.

"Give over," I replied, "You look younger than me! Anyway, there's no harm in a little window shopping, even if you know you can't have the item you really want."

She smiled broadly, and answered, "Never say never Danny, you can get anything you want if you want it that bad."

She wandered off down the shop, I was left staring at her round arse while wondering if I could get back to where I worked without anyone noticing my semi-erect cock in my trousers.

Two days later she approached me. "Neil says you're very naughty for eyeing up his wife, but agreed with the upside-down love heart line about my bum. He says it looks more like it when you can see it without clothes in the way."

She grinned and walked away. I ran after her.

"You told Neil what I'd said to you, wasn't he angry?"

"No, quite the opposite. We talk about anything that anyone has said to either of us, rather than be jealous Neil takes it as a compliment, realising he's married to someone who other people fancy. I'm the same with him too."

She saw my shocked face and continued "We don't keep any secrets, we're a very open couple."

She walked off again, with me now trying to work out if she was giving me cryptic messages. I decided it was my mind trying to pretend she was seducing me, she was happily married after all.

We didn't see each other at work for about a week, then her break time coincided with mine. I sat at a table next to her where she was already sitting with others and caught up halfway through a conversation. There were men and women sitting around the table, and they were teasing a new eighteen-year-old lad about sexual positions. It was obvious he wasn't experienced, as he hadn't heard of many of them. They started talking about their favourite positions when Michelle looked directly at me and asked what position I'd do her in. She giggled as the rest of the table fell silent awaiting my reply.

"Doggy I think, I couldn't resist that arse, especially if you were wearing stockings. Although then I'd miss seeing those amazing tits in the flesh, that would be a shame," I played along with her game.

Her face lit up as the table erupted with comments, and she giggled as she looked around the table. Her break ended and as she got up to walk away she brushed her hand across my lap. She smiled and winked. My mind wasn't playing tricks now, she was definitely leading me on.

I saw her three days later. She looked a little nervous as she approached me, looking around to see if anyone was close by. She leaned into me, her breasts touching my arm.

"Neil wants to know if you want to come around and fuck me?" she whispered, trying not to be heard.

"What? Are you winding me up?" I blurted out.

"Sssh, be quiet, I don't want everyone knowing," she said, continuing to look around. Her breasts rubbed across my arm again, I could feel her nipples stiffening.

She handed me a piece of folded up paper, with her phone number on, and told me to text her when we'd finished work. I couldn't wait until I got home. Of course, I wanted to fuck her, but she'd confused me by telling me Neil had said to ask.

"I'm 100% up for having sex with you, but you said Neil asked you to ask me. Not sure what you mean? Do you want to, or is this Neil making you ask?" I sent it to her. I made myself a drink while waiting for her text reply. My phone pinged shortly after.

"It was Neil's idea, but he knows how much I want to fuck you too. Neil will be in the room, but not join in, he just wants to watch. If that's too weird for you then fair enough, but you'll never get chance again x x x," was the reply.

Neil wanted to watch. Erm, ok. I'd never thought about that at all, maybe they had a behind closed doors secret sexual thing going on. He wouldn't join in. I suppose that made my mind up, although a little awkward at first, fucking someone else's wife while they watched, once I'd got into it I'm sure I'd forget he was there. And she'd said it would be my only chance. I'd spent two years fantasising about sex with her, I couldn't say no.

"Ok then, just tell me what time and when. The first time Neil tickles my balls I'm out though!" I replied, trying to put a jokey mood behind it.

"Phew, you took your time replying, I thought it would be no. I'm fingering myself in anticipation while replying. Neil knows I want to fuck you, just doesn't know how many times I've thought about it," she sent back.

Oh boy. I re-read the message a few times, just to make sure it was real. My phone pinged again.

"Don't get any ideas from that about me leaving him and us running off into the sunset, we're happily married. You just get your window shopping eventually as I told you. 7 pm, Friday."

I sent a message saying that time was great, and did I need to bring anything with me? She replied saying just bring myself, her and Neil would provide anything else.

We didn't have another shift together before Friday. I got home from work, showered, and wondered what to wear. We were only going to be at their house, so I just threw on jeans and a T-shirt, and some trainers. I did, however, have some silk boxers that I rarely wore, so they'd get an outing. I drove over to their house, and opened the gate and started to walk up the pathway, just as Neil and their children came out of the house.

"Just taking these to their nan's where they're stopping overnight," he explained. "Go in and get comfortable, just don't start without me," he grinned.

I waved and told him ok, and tried the door, which opened. I called out for Michelle. Her voice came from upstairs.

"Pour yourself a drink, and do me one too. Lock the door, Neil will use his key when he gets back. Just finishing off getting prepared. Make yourself comfortable in the living room," she shouted down.

The door had led me into the kitchen area, where several bottles of spirits were standing. I knew Michelle liked a vodka, so I poured us both a glass and took them into the living room. I'd gone there in a positive frame of mind, but looking around and seeing so many pictures on the wall of their kids, them all as a family, and some of their wedding day, made me a little apprehensive about how this was going to pan out.

Michelle came down wearing a big fluffy dressing gown, wrapped tightly around her. I was slightly disappointed, I think in the back of my mind I'd thought she would appear and be naked already. The dressing gown was full length, but I did notice some nylon on her ankles and lower legs, perhaps she had put stockings on for me. She pointed at the spare glass, asked if it was for her, and swigged it down in one gulp.

"Another?" she asked me. I finished my drink, handed her the glass, and nodded. She came back with the glasses full. She drank half of hers in one gulp again.

I put my glass down and stood up, leaning forwards to kiss her. She put a hand to my chest, stopping me. "Not until Neil is back," she told me.

I sat back down.

"So, do you do this very often?" I asked.

"No, this is our sixth time I think" she replied.

"So how did this come about, do you guys still have sex or is this a compromise?"

"Oh god no, we probably have more sex together now than when we were conceiving the children," she said. "The only compromise is we both have to agree who we get to fuck. If either of us says no, it doesn't happen. It works both ways."

"So you've watched Neil too?" I asked.

"Yes, it was surreal the first time. Watching him fuck someone else, and getting to see the things he'd normally be doing to me from a different point of view gave it a weird but pleasurable feeling. I came six times the first time I watched him, I think I came more times than the girl herself."

"Have there been anyone else you both knew like me, or is it random?" I asked.

She giggled. "Emma."

"Emma who works with us? Really? She seems so really quiet?" I said, a little astonished.

"The quiet ones are the ones you have to look out for I've always been told. We invited her back again, we've both had her. Separately of course."

"I'm shocked, she's always been really quiet at work, she barely speaks," I exclaimed.

"She's really really good with her mouth and tongue when she starts to use it," Michelle giggled.

Just then we heard a key at the door, and Neil came in. He turned and locked the door behind him.

"Curtains all closed?" he asked Michelle.

"Yes, and everything is out ready," she answered.

Neil looked at me and said despite what was going to happen, they didn't want the neighbours seeing anything. He asked if Michelle had explained the rules while pouring himself a drink.

"Rules, what rules?" I asked.

"Well, you can't tell anyone what goes on, we'll just deny all knowledge, and there's two of us against your word. We like to keep this part of our sex lives very private. Secondly, you can do whatever you want tonight, but remember this is a one-off. Don't regret something then come back for more afterwards, it won't happen."

"Well, Emma happened twice," I quickly shot out.

"Well if you're asking if we can fuck next time, Michelle and I will have to discuss that between us first. I've never thought about men like that though," he answered.

"No, fair point, that's not what I meant at all."

"One night with Michelle. You can walk out now, no problem. We'll just take advantage of the empty house for the night instead," he told me.

I pulled my T-shirt off over my head in response.

"We'd better head up to the bedroom and get a little more comfortable then," Michelle said.

Michelle walked up first with me right behind her, even with her dressing gown on her arse moved gracefully and mesmerisingly right in front of my face. We got up to the landing and she opened one of the doors and ushered me in. Neil followed me and walked over to an armchair they had facing the bed. On the bedside table were several dildos and vibrators of various shapes and sizes. There was also a lifelike strap-on dildo.

Michelle followed us both in and closed the door behind her. She stood facing us, almost like she was waiting for a sign. Neil sat down in the armchair, after re-positioning it a little, and took off his top. He nodded to Michelle.

That seemed to be the sign she was waiting for. She made me stand by the bed, undid her dressing gown, and slid it to the floor. She was dressed in a crotchless bodystocking. Wow, her body was even better than I'd been expecting or imagined.

The bodystocking had small circles that fitted over each thumb, keeping the arms from riding up. Apart from her hands, the only other parts of her not covered in nylon was her head, and her pussy and arse. She turned slowly, showing me what her arse looked like. My mouth had dropped open.

"See Neil, I told you he liked stockings, I think he really likes me wearing this," she exclaimed.

"You look amazing," was all I could muster to say.

"Do I?" she asked, "I've hated how my stomach isn't flat since having the children."

"You're perfect, especially for your age," I told her, trying to make a compliment out of it.

She kissed me on the cheek by way of thanks, then said she needed to see what the rest of my body was like now. She undid my belt and my trousers, then knelt and pulled them down my legs. She smiled when she saw my silk boxers, and I lifted each leg so she could remove my trousers properly. She leaned forward and kissed my crotch through the silk.

"Oh Neil, he really does fancy me, his cock is almost erect already," she told him. I'd been concentrating on Michelle, so hadn't noticed Neil was already naked and sitting watching us, cock in hand now, stroking himself slowly.

Michelle kissed my cock through my boxers a few times, then gently bit on the fabric and pulled them down with her teeth. The waistband dropped enough for my cock to spring out, and it almost hit her in the face. Her teeth loosened as she giggled. She licked the underside of my cock while removing my boxers with her hands.

"Oooh Neil, he's hard, I think he's harder than you normally are," she remarked.

She took my cock in her hand and turned to look at Neil.

"His cock is wider than your's too, he's going to really stretch me with it," she told him.

Our cocks were about the same length, but mine did seem a little thicker, although not that much. I didn't want to spend the night looking at Neil's cock though.

"Just one quick question before we start getting into it, it's not a question of coming and leaving is it?" I asked, "Only I'm fairly sure I could manage three or four times with your wife."

"That depends on your stamina levels," Neil answered, "although you're not staying all night," he said laughing.

"Just so we're clear, that's all," I said. I looked down at Michelle. "I want you to make me come before we start to fuck."

She smiled up at me and grabbed the base of my cock. She took me into her mouth, little by little feeding it in until she had engulfed my entire length, making sure it was coated in saliva. She started to suck me with long slow strokes, cupping my balls with her spare hand. My hands went to the back of her head, but I let her stay in control. She continued to suck me for a while, then took her mouth off me and started to lick my balls. She licked all around them, especially around the underside, then asked me to turn around and bend over the bed.

I did as I was told, and she reached between my legs and started to wank my cock, pointing it downwards like she was milking a cow. I felt her breath on my arse and her tongue on my arsehole. I jumped a little, and she told me to relax and I'd get used to it. She continued to rim me, making sure my arse was lubricated with her saliva, every now and again dipping her tongue into my arse. I'd never had this done before, and although it felt strange it felt really good too.

She was wanking me with slow strokes, and I felt a finger on my arsehole. It was very wet, she'd been fingering her pussy to get it wet enough. She pushed her finger up my arse, letting me get used to it until she was pushing her entire finger in and out of me like a mini penis.

"Do you like that, or should I stop?" she asked.

"It's weird but very nice," I told her, "but I think you're going to make me come quicker if you carry on."

She withdrew her finger anyway and turned me back around. She fingered her pussy again, put her hand between my legs, and inserted her finger again. I gasped, just as she put her mouth back on my cock. She started a rhythm where when she engulfed my cock, she pushed her finger up me. God, it felt good. It was still weird having something up my arse, but I didn't want her to stop.

It only took about five minutes before I told her I was going to come soon. She quickened her pace a little, then in one swift movement withdrew her finger and mouth from my arse and cock, and used her hands to grip my cock with her big tits. My cock disappeared until she started to tit wank me. I had been close anyway, but the feeling of her nylon clad tits rubbing my shaft soon had me shooting my load. When she felt me coming she squeezed extra hard, spurt after spurt hitting her chin and soaking the neck and upper chest parts of the bodystocking. I slumped back onto the bed.

"Oh Neil he's come so much, it's a good job he didn't come in my mouth, he might have drowned me," Neil grunted as he came all over his legs. He didn't move from his sitting position.

Michelle started to wipe the come from her neck, putting her fingers in her mouth.

"He tastes so nice, maybe it's a pity he didn't come in my mouth, it's almost a waste for it to be on me instead," she told him.

She leaned forward and licked my cock clean, coaxing me into another erection. I stood up and pushed her onto the bed.

"Your turn now," I told her.

She manoeuvred herself diagonally across the bed, so Neil had a better view. She hitched up her legs as I buried my head between her legs. I started to lick at her clit like my life depending on it, as I felt her body start to tremble more I slowed right down. I put my hands on the back of her thighs and spread her legs further, then started to lick at her arsehole until it was wet. I went back to licking at her clit, deliberate flicks that barely touched it, but enough to make her body arch. I put two fingers into her pussy, then switched and put them into her arse. She squealed with delight.

I kept this up until her arse was fully lubed, then split my fingers so they looked like a Vulcan salute. I inserted two fingers into her arse, the other two into her pussy, and proceeded to finger fuck her. She groaned loudly, her body almost in two as her back arched. I gave her about twenty seconds to get used to it, then started to lick her clit again too.

"Holy shit Neil, this feels good, very very good," she cried out, in between moans of pleasure. I thought the whole street might be able to hear her.

"Fuck, Neil can you see, he's fingering my arse and pussy at the same time, oh shit it's good." Neil came all over his legs again.

Michelle was squirming like mad underneath me, and she shook violently as her orgasm ripped through her. I kept on fingering her as she came, her juices squirting over my face and hand. I stood up to give her a chance to relax, when she had done she sat up, took my hand, and licked my fingers clean. She took great delight in tasting the ones that had been in her arse.

She asked me to lay down on the bed, and stood up by me, making sure we were facing Neil. She climbed into a kneeling position on the bed, straddled me, and reaching behind her guiding me into her soaked pussy. On the second stroke, she was fully impaled on me. She looked over her shoulder at Neil.