Their First Cuckold

It had been another hard shift, busy and with enough customers complaining to make us think about giving it all up. That's life working in a shop I suppose, it's part and parcel of the job. I thanked my team, started laughing and told them I'd see them tomorrow for more fun and games unless it was their day off.

Part of my job was to supervise the checkout area. It was quite a big shop so there weren't many times when we didn't have people queueing to pay for their shopping. In between, I tried to have a laugh and a joke with the staff to keep morale up. Most went along with it except for Brook. She was the quiet one, one of the younger members of staff, who seemed content to get through her shift without fuss.

When I say younger, she looked it too. I knew she had just turned twenty years old from the documentation she'd bought with her as proof, and from setting up her payroll. She was all fresh-faced but pretty in a plain kind of way. 5' 4" tall, with dark hair always in a loose ponytail. I tried joking with her, but most of the time the most I got back was a smile and then she'd look away. Maybe she just didn't get my sense of humour, most of the others were in their fifties like me after all.

I'd been sitting eating my dinner in the canteen one day when I saw her on the far side, sitting with her boyfriend. I knew who he was as I'd seen him picking her up after her shifts sometimes. They were whispering, but I saw them both keep looking over. I went back to looking at my phone, trying not to keep looking up, when heard a noise and looked up to see Brook standing by me.

"Hi, Danny, sorry to bother you. I'm off for a few days now, if I give you my number can send me my rota for the weekend please?" she asked.

"Yeah sure," I answered, "I'll need to look at it anyway as we have a couple of people on holiday so might need to swap some shifts around, I'll send it to you as soon as possible."

I handed her my phone and she typed in her number, smiled when she handed it back, and then walked back to her boyfriend. He had a big smile on his face and when he looked over, I put my hand up and he gave me a thumbs up. I went back to my phone, then a few minutes later heard footsteps coming my way.

"Brooke will do a late shift on Saturday if you need her to," Pete, her boyfriend told me.

I looked at Brook who smiled back at me, telling her I probably would need her on that shift anyway as I thought there were only two other staff in. She told me no problem and they walked off. It was the most conversation I'd had out of her in the month that she'd worked with us.

After finishing my break I was in the offices checking the rotas and was right, apart from myself there were only two staff in. I looked at the time and realised she'd have left now, so I sent Brook a message telling her about doing a late, and she replied almost instantly saying no problem, with three smiley faces.

Getting home later I opened the door just as my wife Stacy was ready to leave. She works as a midwife and most of her shifts are overnight, she never complains as she gets a good shift allowance on top of her normal wage.

"Oh, I thought we'd have an hour together before you went in," I said, grabbing her hips and pulling her to me.

"Sorry babe, Susie went home sick so I'm going in a little earlier, I'm sorry now too," she giggled, feeling my cock pushing against her thigh.

I'd had something to eat and had settled down to watch TV when my phone pinged. I picked it up, thinking Stacy might have forgotten to tell me something before she left.

"Sorry I'm quiet at work, I'm wary of people when I first meet them," the message from Brook read.

"It's not a problem, there's too many loud people anyway!" I sent back.

"I'm easier to talk to when I've gotten used to people when I know I like them," she replied.

"You like me then?" I asked.

"Yeah, you're funny, and a nice person too. I've always liked you, I just needed to feel comfortable to interact that's all," she answered, "Pete says it's just me not being confident in myself."

I carried on watching TV, flicking channels to find something else to watch. Fifteen minutes later my phone went off again.

"Do you like me too then?" she'd asked.

"Yes, you're a very good member of the team," I replied.

"No, I meant do you like me, like find me attractive?" she asked.

I read the screen two or three times. I wondered if it might be Pete texting instead.

"You're pretty, your boyfriend is a very lucky man," I sent, in case it was him.

I didn't hear anything else for the rest of the week. Saturday evening came and walking back to the checkouts from the offices I saw Brook already serving customers. As I got there a customer walked up and told me they'd accidentally broken a vase and apologised. I thanked them for letting me know and sent someone to clean it up before someone hurt themselves on it.

Nobody was queueing a little later on, and I asked Brook if she'd be okay on her own while the other two went to tidy around the shop. She smiled and said she'd be fine if I stayed there with her. The others gone, and serving nobody, she started sweeping around the checkouts. I didn't notice at first, she did keep looking back at me and I didn't know why until I saw exactly why.

The work uniform is T-shirts with the company logo on them, staff are told to wear black trousers and black shoes, although a few wear trainers and we're lenient not to bother telling them not to. Brook had black trousers on alright, but they looked sprayed on they were that tight. As she swept her t-shirt had rode up onto her hips, jiggling with her motions, her arse pointing directly at me.

I couldn't stop staring, her hips were a little wider than I'd noticed before, her round full buttocks merging down onto slightly plump thighs down to perfect calves. My eyes searched back up to her arse, noticing that not only were her knickers visible through the stretched fabric, but so was the label on them.

I heard giggling as she turned and went back to her checkout, smiling as she walked past me and called a customer to her. Once served, she looked over at me.

"You shouldn't really be wearing those trousers," I told her.

"Well they are black, that's all we were told. You seemed to like me wearing them in them anyway, I saw you looking," she giggled again.

"Hmm, I can't argue with that, guilty as charged," I laughed, "but a word of advice, cut the label out of your knickers if you do wear them again, and maybe smaller less visible knickers."

She turned and look down over her shoulder, then frowned.

"I didn't think about my knickers showing," she said, "but thanks for your feedback," she laughed.

We didn't speak much as the others came back, and then we shut the shop and went our separate ways. I woke the next morning to a message. I looked over, Stacy was still at work.

"I took your advice," it read. There was an image attached, I clicked to open it and there was Brook's arse, in the same trousers as last night, with no visible knickers nor label.

"Much better," I sent her.

I had a shift later that day and Brook was already in. She had on normal trousers today as it was busier during the afternoons, but when she got the chance she asked if she was working late on Saturday again, Pete had asked if I could drop her off as his car was playing up. I told her I didn't see the problem and by the time I got home Stacy would be at work herself anyway.

Later on, after getting home, Brook sent me the same picture.

"Because you didn't get a chance to see them today, in case you were missing them," she'd sent with smiley faces.

"Do you still think I'm pretty then," she sent before I'd replied.

"Very nice, have you actually got knickers on under them?" I asked.

Another image came through, her trousers pulled halfway down her buttocks revealing a black g-string.

My phone pinged again, this time the trousers were right under her buttocks, Brook was bent over, just the tiniest piece of fabric covering both of her holes.

I looked at the pictures a few times, my cock stirring in my trousers. Suddenly I noticed something.

"If you're pulling your trousers down, who's taking the pictures?" I asked.

"Pete of course," she sent back.

"Does he know you're sending them to me?" I asked.

"Yes," she replied, "sorry gotta go, speak later."

I saw Brook fleetingly when our next shifts briefly overlapped but did have time to notice she wore her normal trousers. Saturday seemed to take forever to come around, then finally she turned up, tight trousers on. She smiled broadly at me as she saw me, but then went back into quiet mode around other staff members. There were only five of us in tonight, but the shop wasn't busy anyway. The others had gone off to do various jobs, leaving just Brook to mind the checkouts.

"Did you like the pictures then? I'm wearing the same g-string today, Pete bought it for me," she beamed when she noticed nobody else was about.

"Pete's a very lucky man, you have a great arse," I answered, "and he doesn't mind me seeing them?"

Brook blushed a little, then told me he'd encouraged her. She saw a look of mild shock on my face.

"He's trying to bring me out of my shell, to be more confident in myself, to try new things," she said before turning away sharply as she blushed again.

"Are you still okay to drop me off later, I forgot to check with you," she asked.

"Yeah, it's not a problem, Pete's car still not fixed then?" I told her.

She shook her head, and then a mixture of customers to serve and staff coming back killed the conversation off.

The shift now finished, she waited for me to lock up and then followed me to my car. She threw her bag and jacket on the back seat, saying that although it was quite warm she'd bought the jacket in case she'd had to walk home. Getting into the passenger seat, I noticed she'd tucked her t-shirt into her trousers.

Brook was quiet for the first few minutes, looking out of the passenger window. I kept looking over at her, noticing her breasts jiggling as he drove down the bumpy roads. I asked if she was okay.

"Yeah, sorry, I wanted to ask you something actually but I'm plucking up the courage to ask, I don't know what you'll say," she blurted out.

"You can ask me anything, it's fine," I answered.

"Do you really like me, like, find me very pretty?" she asked, blushing as she did so.

"Yes, you're beautiful, I told you Pete is a lucky man, you just don't see it because you doubt yourself," I replied.

"Beautiful enough to fuck me?" she said abruptly.

As she said it we stopped at traffic lights. We sat, staring at each other in silence.

"I knew I shouldn't have asked," she whispered.

"It's not that I wouldn't. but you have a boyfriend and I'm married, and I wouldn't want it to get awkward at work," I answered as diplomatically as I could, my erection at the thought of fucking her disagreeing with me.

The rest of the journey was in relative silence, and the only talk was far removed from the conversation, more about work itself. As we pulled up outside her house I saw Pete open and stand in the doorway, watching.

"I'll just get my things out of the back," Brook said.

I told her I'd wait and expected her to get out and open the back door, instead, she took off her seatbelt and leaned between the seats to reach into the back. Her round arse was right by my face, just the tight black fabric between me and her hidden gems. I wanted to move my head, playfully pull the fabric with my teeth, to slide my fingers along the crack between her buttocks where the fabric disappeared, but knew Pete was looking on. She seemed to be there for an eternity.

"Sorry," giggled, "the handle of my bag is stuck on something."

Trying to pull the bag free made her body jolt backwards, and an image of me behind her naked self, that round arse pushing back onto me as my erection slid into her, flooded my head. My erection was bursting to be set free, and then her face reappeared, all flushed and red.

Brook thanked me for dropping her off, and then got out of the car. Walking towards Pete I saw him mouth something, then Brook shook her head to say no. Pete looked towards me, a disappointed look on his face but he waved goodbye and gave me a thumbs up, presumably for dropping Brook home.

I got home and went in to silence and a note from Stacy saying she'd gone in to work early again. It was more of a pity tonight, despite me not complaining as she got paid extra for overtime, my cock needed some action after having Brook's arse in my face earlier. The thought of it made my cock twitch again. Not only that but her asking if I'd fuck her too.

Me. In my fifties, balding with grey hair and a pot belly. This young, quiet, but round-arsed girl had asked me to have sex with her. I mulled it over in my head, trying to work out why. I know she was quiet, awkward even, but she was pretty enough that guys her age would be interested in her. Pete was her age after all. I wondered then if Pete knew about this new arrangement.

I was halfway through watching a film on TV when my phone pinged.

"Sorry about earlier, hope we're still mates," Brook had typed.

"It's no problem, it's forgotten about, there'll be no problem at work. You're beautiful, but it wouldn't be fair on Pete would it?" I responded.

"Fair? It was Pete's idea," Brook had replied with a smiley face.

"What do you mean Pete's idea?" I sent back.

There was a little bit of a pause before a new message came through.

"He wants me to fuck someone else, to make me see someone else fancies me. I've only ever slept with him, and he thinks this will help me become more brave, more out there," she replied.

"He's encouraging you too? Wow, that's a big step, he must be very trusting in you then?" I asked.

Again, another pause, it was almost five minutes before a reply came through.

"It's not so much in trust, he'll be there watching. Don't take this the wrong way, but he thinks you'll be perfect," she written

"He wants to watch eh? Fair enough. What do you mean I'd be perfect?" I responded.

"Well, you're married so you're highly unlikely to tell anyone. And he doesn't see you as competition," she said, "sorry if that sounds harsher than it should."

"Competition?" I put.

"He thinks if he lets me sleep with someone our age, I might be tempted to stay with them afterwards. He thinks with you it will just be a bit of fun," she messaged.

I didn't answer for a while, around fifteen minutes passed before my phone went off again.

"Do you need some persuading then, hope this helps."

There was an attachment with the message, I clicked it and Brook's arse came into view, her trousers halfway down her thighs and her g-string cutting into her buttocks. Around thirty seconds later a second message, no text but another attachment. This time the trousers and g-string weren't in shot, but her hands were, pulling her buttocks apart and exposing her holes to me.

Her arsehole was tiny, a light pink colour like a little rosebud, despite her pulling her buttocks apart it barely opened. Her pussy was much the same, very neat, with no big protruding labia everywhere, like they'd all been packed neatly away. Her hands in the shot told me Pete had taken the pictures.

"Very nice, when did you take those?" I asked.

"Just know silly, Pete said he thinks it will change your mind. Do you still need convincing?"

I hesitated before answering and decided to push my luck.

"Yeah, I need more convincing than that, and show me you're doing them now too," I asked.

The next picture was Brook lying forward on the bed, arse pointing directly at me as her feet were planted on the floor. Her hands pointed towards the TV, the programme on it had the station in the corner. I quickly changed my TV to that channel just in time to see the same scene just finishing.

Another message, this time Brook was lying on her back, legs spread and pointing right up, holding today's newspaper across her stomach. I could see now she was enjoying this, as the first signs of her pussy being wet showed.

"Convinced now?" she asked.

"Not quite," I replied with a smiley face.

A similar picture came through, still on her back but with two fingers now in her pussy. Her top half was covered with a long-sleeved jumper, that was also pulled up over her face.

"Camera shy?" I asked.

"A little yes, it's my first time doing anything like this too," she said.

"Pete said if you're still not convinced, can I phone you if your wife isn't in?"

I wondered what my wife had to do with it, but told her yes anyway. The pictures had already made my mind up, but I was intrigued now. I wondered what she'd say, probably tell me to stop dreaming that this young pretty thing wanted me. We'd had encounters with others while we were younger, always telling the other either before or after, but those days were long gone or so we'd thought.

My phone rang, it was a video call. I answered it and saw a hand moving the phone. I turned mine sideways in time to see Brook's arse move away from the phone. She walked towards their bed, and I saw her arm jerking, until she turned around, facing towards the screen.

Brook parted her legs and used one hand to lift her jumper a little, holding it to her stomach. I couldn't see much further up with the angle that the phone was at. She lifted one leg a little, Pete was lying on the bed. Brook held his erection, not that big at around six inches long, and slid herself down onto it. It took her a while to take him in, her loud groans telling me she was a tight fit, but eventually, she was sitting with him all inside her. My view was his legs and cock, with her legs on either side of him, and the base of her stomach.

Brook started to ride him, slowly, groaning loudly each time she sank onto his cock. I watched intently, staring at her pussy, instinctively releasing my cock from its confines. I stroked, matching her rhythm, her hands on his knees.

"Can you see me?" she asked in between moans.

"Sort of, I can't see your face though, but I thought you'd done that on purpose," I answered.

I watched as she slid herself off Pete's cock and walked back towards the phone. She moved to the side of it, and the screen moved a little. I could see Pete now looking towards the screen.

"That looks better," I told her, "put your feet up on the bed too."

I saw Brook walk back towards the bed, turn and smile at the camera. Taking the same position as just, she eased down onto Pete's cock, this time a little easier. She turned and said something to Pete, whose hands appeared on her hips. I assumed it was to steady her and she lifted her legs one at a time and planted her feet on either side of Pete's legs.

She started riding again, her face screwed up, biting her lip as she rode him. She started getting quicker, her mouth opened wide as her moans and groans got louder. Her hair was down, billowing about as she moved, it made a change from being tied up.

"Lift your jumper," I shouted out.

Brook did so, and I gasped. Like her arse seemed too big and round for her small petite frame, so did her heaving breasts. She couldn't have been more than a 30 or 32, but those were big round and firm, at least a C cup. The works uniform certainly hid them well. She played with her nipples with both hands, tweaking them, and now and again putting her fingers into her mouth to wet them, and then rubbing her nipples until they were both erect and large.

Her jumper kept slipping back down while her hands were busy, and before I got the chance to suggest it she lifted it up and over her head, throwing it on the floor. Now her hair mischievously covered her breasts, and she used her hands to rub it across her nipples, eventually pushing it back behind her shoulders. Each time she loosed it, the force of her riding on Pete made it fall back in front of her, and each time she'd grab it and hold it above her head, not once breaking her stride.