Younger Coworker’s Secret
An SPH Experience by Jill.
Okay, so when I joined the team, there was this younger man who worked with me and showed me the ropes. He was always very helpful, and we’d gotten pretty close. Each day we’d work hard together as more and more work kept coming in, but Ryan was always calm and attentive, and despite the increasing workload, we had a lot of fun. Over a few years, people in the team moved on, and others came in, so in the end it was a team full of ladies and this younger man, Ryan.
We always had fun on nights out, and Ryan and I were like a wee double act. As the new ladies joined the team, the girls started to organize coffee mornings, just 2 or 3 of us ladies at a time, some days before work, and we’d get chatting about things, life, and family problems. But after a while, the ladies started making a few comments about Ryan. They said it was pretty obvious that he put me on a bit of a pedestal. They said he worshiped me. They’re words, not mine. So all the ladies were asking me, Jill, what are you going to do about him? At the time, I was in my late 30s and married, so I said he needed a date. After we’d all been talking about it, they decided we should set up a profile for him on a dating site.
I know him and said he’d go through the roof if he found out we’d made a dating profile for him. But in the end I was outnumbered, so I gave in. I got some pictures of him, and they made the profile. I revised what they wrote to avoid a negative tone. Anyway, we got it sorted out, and they agreed I could make some changes to the profile. The hard part was knowing what to do if we got any matches.
Well, that wasn’t as big a problem as we thought. I knew they should have let me change more of what they’d put on his profile. He’d had no matches after a week or so, so it was a bit boring. So one girl on the team, Laura, told her friends about it. Some of her friends use that site anyway, and in the end she got one of them to agree to go on a date with him. But then we had to think of a way to get them to meet without him knowing what we’d done.
I was able to find out where Ryan was going out over the next few weekends, and we found a place where Laura’s friend could meet him “by chance”.
Anyway, next week, after the chance meeting, he came into work one day wearing a nice jacket, and I was asking him, “Are you going anywhere nice?” and he wouldn’t tell.
I made sure the others settled down and didn’t quiz him, or he’d know something was up.
So anyway, he was just going for coffee with her that evening after work, and they had another coffee date before meeting up for a proper date on Saturday night.
We asked Laura to text the girl and ask her to share all the details about him.
And Laura always goes too far, so she said, “We really want to know everything…” lmao.
Anyway, Laura’s friend goes on the date, actually calls Laura during it, and then Laura updates us all in DMs on Saturday night. We were all rofl.
So anyway, she’s stringing him along and reporting back to us, well, through Laura, and agrees to meet him during the next week and then ends up going out with him the next Saturday night too.
So Laura keeps pushing the girl to get more info about Ryan and what he does on a date, and she’s telling her things about him to see what she can get out of him. Well, this girl is obviously like Laura, and she takes it too far. She goes on the date, then they bump into a few of her friends at a bar later, and they get him really drunk. Anyway, being Laura’s crazy friend, she takes him home with her, but none of us know this except Laura til we were all in work on the Monday morning.
Anyway, she had sent Laura some messages about the night. So Laura waits until Monday, and when Ryan leaves the room for tea break, she gets really excited and tells us we need to be quiet and look at our phones. So Laura forwards a message to all of us in a new ladies-only group chat that he’s not in.
So anyway, all the phones are buzzing at the same time, and Laura has a massive grin on her face, then says to us, “Tell me when you’re done.”
We are all reading, and the message basically says What a fucking loser. Why did you set me up with him? When we got back to my place, he was sooooo drunk. I got him to play truth or dare to get more answers to your list.
I didn’t know Laura had sent her a list of questions to find out personal things about him, but the others seemed to know.
So anyway, she says the truth column, found out he has a foot fetish and loves women in boots and high heels, he’s a VIRGIN, and he has a thing for someone he works with.
Laura was like, we all knew that last one, JILL.
Then it was the dare column.
First dare, she dared him to get naked for her, which he did.
Second dare, she dared him to let her tie his wrists to the bed. And he did that too.
By this stage we were already gasping and pmsl. Like seriously!
We were all in hysterics, then Laura says, “Are you all done?” and sends us more messages: 2 pictures with a message beneath each. The first one is him tied to the bed, full body with face, totally naked!
The second one is Laura’s friend laughing with her little finger beside his little man, same size OMFG!!! So shamed, lmfao.
Then there was the message below with the pics forwarded from Laura’s friend. It said, “It was tiny; when I laughed at it, he shot his load. No touching.”
I was speechless, really, so shocked, no words. Then they all started looking at me, OMG, then I started pmsl, I mean seriously! I said to them omg did you see it? He was hard in both pics.
She said it was the smallest she’d ever seen. I still have the pics; it was really skinny and a bit crooked. Oh, and the head was skinny too, no mushroom head. So she said, obviously, she didn’t sleep with him, so he’s still a virgin.
She said he kept staring at her boots and was really nervous. It wasn’t until the drunken truth or dare that she realized why he kept looking down at her boots all night. She said she could get him to do anything, couldn’t believe he let her tie him up, told him it would be sexy. So she did and then took the pics. He begged her to delete them and not tell anybody, so she eventually convinced him that she wouldn’t. She deleted the pics in front of him but had already saved them to the cloud.
And she didn’t tell; she sent us them instead, lmao.
Well, all day in work we were sending each other messages and making comments in front of him; he didn’t know what was going on. It hasn’t really stopped tbh. He didn’t have a clue the girl was friends with Laura.
Thank god I’m not dating anymore if that’s what’s out there. The others were trying to go early and then get me to tell him while they waited outside the door, but I didn’t. They did get me to wear my boots into work on the Tuesday and to pretend I had hurt my ankle. I got him to massage my foot at my desk during tea break. The others left us alone so I could ask him, and they were standing outside the door behind him, looking in. I was sitting on my chair, took off my boot, and placed my little foot on his chair between his legs, just past his knees, as he massaged it. I thanked him so much, then told him it was a bit sore further up my calf as well, and got him to rub that too.
As he leaned forward, I moved my foot further forward til it was very close to his crotch. He’s being gentle and rubbing my ankle and up my calf, and after a while I’m like, oh yes, Ryan, just there. This is still when he’s massaging my calf, and I point my toes forward, pushing my foot down onto his crotch. He started to recoil, and I said, don’t stop, please, just there, Ryan. Well, poor little man, he couldn’t help himself and kept rubbing my calf while I’m wiggling my toes and pressing them against his little dick, ooohhhhing and saying oh that feels so good. Honestly, I could feel his little man getting hard, but it was like there was nothing there; it was tiny, couldn’t even see a bulge. I was trying so hard not to laugh, and when I did, I told him it was just tickly.
Anyway, the girls eventually burst in, pretending they were chatting about something else, and he stopped immediately. I said thanks, it feels much better, and then put my boot back on. He tried to make it look like he wasn’t watching, but I could see him looking as I slipped my little size 3 1/2 foot back into my boot. Later on, I thanked him again, touched his thigh, and asked him if he would do it again tomorrow morning when the others were in a meeting if my ankle was still sore. I bet he was hard all night just thinking about it.
The next day I wore my little black ankle boots with a very high heel, which he really liked, and he got him to do both feet, calves, and even a bit up my thighs. Honestly, he was in heaven, especially when my little toes pressed down on his little man again. I’d just say something slightly suggestive while I was doing it and he couldn’t speak, pmsl. Even took a quick sneaky video of it when I got a message on my phone. I showed the girls when he was out for lunch, seeing if we could see him O as I pressed my toes down, haha.
We’ve talked about doing a Secret Santa at Christmas. Then one evening, one of the ladies sent an instant Facebook message to our private group chat with a picture of the special gift we could get Ryan for Secret Santa; we were all in fits of laughter. She’d found this big reindeer thong. Shileen said, “Look at the size of it.” I said I’d be at the bar when he’s trying it on, but they convinced me later. They said, “Doesn’t matter who gets him in the drawer; we’ll get it as his gift anyway,” lmao. It’s going to be hilarious, and I can keep some mini condoms and a tape measure in my purse too. If we get him drunk enough, I know I can make him try it on just for me in the loos. Then I’ll text the ladies so they can all come in and see the show too. Oops, accidents happen. See how much he can fill that reindeer, ha ha; see if the sad little nose droops. He’d be so shamed, lmfao. Can you imagine? I bet that would get his little man to pop again—no touching, OMFG, seriously, pmsl.
If he only knew that we had seen those pics of his little man. It’s hilarious, and we’ve all shown them to our friends. Can you imagine finding that little thing when you get him back after a date? Omg Ryan, seriously? It’s tiny.
If you ever read this, you know we all know about your little secret, Ryan.
Love, your crush,
Jill x
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