Jessica’s First Time with her Co-Worker
By ohionewbie96.

Jessica is a very appealing woman by all accounts. She is 31, 5’9” and about 140lbs. Tight body, 34C boobs, a nice but modest ass, and legs that run for days. I, Michael, am 30 years old. I’m about 5’11”, 210lbs, and have a 5” penis with average girth.
Our sex life has never really been bad, and I think that is the main reason she has been so hesitant to pull the trigger. Why risk something when she’s content with what we have in the bedroom? However, we have toys that put my manhood to shame. Most of them are longer, with considerably more girth on them. Every time they are used, she always gets off faster and harder than when I’m with her. She’s only ever had a legit penetrative orgasm from the toys, whereas with me the only way she can get off is if she’s on top and grinds her clit on my pelvis for stimulation.
I always brought up to her how much more she gets off on the bigger toys, but she always results to saying she enjoys the intimate aspect of real sex more, even if the toy may “feel” better. To that, I’ve teased her for a while that that is the reason we need to bring someone else into the bedroom, to which she will usually just laugh off and disregard.
We have also played with chastity cages before, which she enjoys the power it gives her for a short period but then results in allowing me out of the cage to have sex and eventually finish, causing the cage to go back in the dresser for a few weeks before the cycle repeats itself.
Now that the image is painted and there’s some backstory, we get into the events that transpired.
The time came again where I brought up chastity play, and, like usual, she agreed it was a good idea and told me to have myself locked up with the key on the dresser by the time she got home from work. This was the usually process for how this played out, so with some finagling of the cage to get my average sized penis compressed into this small 1” long confined space, I did as she asked.
Jessica got home from work around six p.m. and verified that I satisfied her request. The rest of the evening went as normal. Dinner was cooked, dishes were cleaned, etc.
It was time to get into bed and mess around like usual when the cage was involved. We snuggled up and started making out for a bit before I eventually made my way down between her legs. I enjoy eating Jessica out; it’s one of my favorite things, and I’ve always told her that. When I got down there to start going to town, I noticed it was a little wetter than usual but chalked it up to the chastity play. After about 10 minutes or so, I brought out one of our toys that put my cock to shame and started putting in work. She came once and said, “Okay, your turn!” with a big smile, again, per usual.
I got out from between her legs, and she motioned for me to lie down on the bed to unlock me. Once she got it off, she straddled me and slid to the base in one motion. It felt incredible, I always throughly enjoy the feeling of her after she’s been stretched out by the larger toys and it usually results in me cumming faster than I do on a normal basis. I thrusted in and out feverishly for about 45 seconds before I mustered out between my pants “I’m gonna cum soon!”
“No! No, you’re not!” Jessica exclaims as she hurriedly hops off of my cock, ready to blow at any point.
I look at her with some confusion, as I was on the verge of climaxing, and say, “What??? What do you mean no?”
She looks at me with this grin on her face and says “you always tell me that I’m supposed to be the one in control of your orgasms and once I’m done with your cock I don’t need to go along with it until you cum, so no. You will not cum!” as she grabs the cage to put back on.
I was speechless and didn’t have a good rebuttal because she was right. I always tell her after the fact that that is the point of the cage, but every time in the moment even if I want her to say it mentally my cock does not want to stop. She could tell this turned me on even with my shock because my already stiff cock was getting even harder as she tried to navigate the cage onto it.
“See, don’t act like you don’t like this,” she said with a devilish smile. You will keep it on all night and tomorrow while working from home. Tomorrow evening, we will go to dinner, and you will have it on then, and maybe after dinner, if you’re lucky, I’ll take it off!”
I was so turned on by what transpired that I did as she said without question and pushed back. The night was frustrating, as I woke up a couple of times very strained, but I could make it through.
The next morning, I woke up as she was about to leave for work. She kissed me and said, “Make sure that little thing stays locked all day!” as she patted it and walked out the door.
My mind was racing all day as I was so horny. Constantly readjusting to try to make myself more comfortable but my cock was pushing at the walls of the cage the entire day. Around 1 pm I get a picture from Jessica and open it to find a selfie of her lower half with her panties pulled to the side showing her glistening slit. “Don’t forget the prize for being a good boy,” the text that followed said.
Jessica got home from work around five and said we needed to prepare quickly because we had dinner reservations at a nicer restaurant at six. I got ready in the bedroom and went into the bathroom to see her dressed in this tight black dress she had worn for a while but never really wore because she felt it was too revealing.
“Wow,” I mutter, “you look incredible!”
“Thank you, hunny. I thought you might like this dress on me,” she says, looking at me in the mirror.
We pull into the restaurant and walk inside just in time. Jessica approaches the hostess and says, “Reservation for Jessica!”
“Uhhh oh yes, reservation for 3?” The hostess replies.
I reply to let her know it’s only 2, and Jessica cuts me off: “Yes, that’s right!”
Just as I look at her to question it, she looks over my shoulder and says, “Jake! Right here!” I turn around to see her longtime coworker, Jake.
I’ve known Jake from different work events over the years. He’s an attractive guy with clean-cut facial hair. He stands about 6’3” and has a body that clearly shows he works out most, if not every, day.
“Jessica, how are you!?” Jake says as he hugs her. “Mike, long time no see!” He turns and says to me, extending his hand for a shake, which took me off guard by the firmness he displayed in my hand.
“Hey, Jake. Yeah, it’s been a while.” I say, confused as to why Jake is meeting us for dinner, especially considering I thought it was a nice dinner between us tonight.
Just then, I feel I twitch in my pants, reminding me of the steel barrier secured tight around my flaccid shaft hidden under my pants. There’s no way this is what I think it is. It must be some last-minute thing, or they needed to discuss something for work tonight. But what about what she’s wearing? She never wears stuff like that. My mind is racing as we are taken to our table.
We are taken to a four-person table, with two chairs on one side and one on the other. I go to one side of the table and pull out a chair for Jessica to sit down, and she gets close to my ear and whispers very quietly, “Yeah, the thing you’ve been wanting? It’s going to happen tonight with Jake. So sit there and be a good boy; that cage better still be on!”
I’m sure Jake didn’t hear what she said, but from the look of it, he knew exactly what was going down tonight. He’s got this smug, smirky look on his face when I look over as he pulls the chair beside him out for Jessica to sit down.
Dinner went well, by all accounts. My mind was constantly bouncing back and forth between whether this was a bad idea and how hot it would be for it to happen. I couldn’t focus on most of the conversation as I tried everything to keep myself from busting through my cage.
The bill comes, and Jake covers the whole tab. As we are walking out, Jessica looks at me and says, “Hey, I’m going to ride back to the house with Jake. I’ll see you back there!” as she kisses me on the cheek. I couldn’t even get anything out of my mouth before they headed for the door.
I was on the edge of my seat the entire drive back to the house. My mind is going to a million places at once. I can’t believe this is going to happen. Maybe they’re messing with me?
I pull into the house right behind Jessica and Jake, and they both hop out of his car, seemingly eager to get inside. As we get inside, she tells Jake where the bathroom is, comes back to stand in the living room, and gently kisses my mouth. Her mascara is a little messed up, and her hair isn’t as well-kept as when we left the restaurant. Did she give him a blowjob on the way home??
“So, I hope you’re not mad, but I’ve been thinking about this for a while now, and Jake has kept making hints that he finds me attractive, and I thought this would be the perfect time to do it!” She says to me, quickly and excitedly. “And Michael… his cock is massive… I know you’ve been saying you would like that most for me; I just wanted to give you a forewarning.”
“How do you know his c…” I stop my sentence as Michael exits the bathroom and walks towards us.
“Hey champ, how did my cum taste?” Michael says to me with an arrogant tone and a smirk, turning to Jessica before realizing she hadn’t told me because she was blushing hard. “Oh, you didn’t tell him? Yeah, your girl gives some great head, man. Didn’t take long to get me off on that drive home!”
I’m in shock as he says this, and I look at Jessica, who has an embarrassed but not sorry look on her face.
“Hey listen, Michael. I’m down to give your wife a good time, but I find it a little weird when other people watch me, so I hope you don’t mind hanging out here in the living room until we’re done,” Jake says to me, motioning Jessica to the bedroom.
“I’ll meet you in there, Jake!” she says to him and waits for him to enter the room. “Sorry, I hope you don’t mind not watching?? He told me that before, but I didn’t think it would be that big deal.”
“Uhm, yeah. Yeah, that’s fine. Is that what you want?” I stutter, saying back to her.
“I need to have him inside of me… it’s so thick and long, our toys don’t even compare…” she tells me.
“Really? Uh, yeah, okay. Yeah, that’s fine,” I reply.
“Okay, yay!” She says, joyfully getting on her tippy toes and giving me another kiss. “I love you!”
“I love you too. Don’t forget the condoms are in the bedside table drawer!” I say as she’s turning the corner into the bedroom and gives me a thumbs up.
The door closes to the bedroom, and now I’m stuck sitting there in the living room with just my imagination and a cock ready to break out of the cage.
They turned on music in the bedroom, so even if I had wanted to eavesdrop, it would have been hard to make any words out. After sitting there for probably 30 minutes and heard different muffles of moans and grunts, I got so horny that I took my pants off and started to try to touch myself through my cage as much as I could. A giant wet spot of precum had already appeared on my underwear, and I was itching to get a full release because my balls were beginning to swell.
I sat there for probably another hour doing the same thing, just touching what little bit of skin I could through the bars in my cage, wondering how much longer this would last. Finally, the door opened, and Jake walked out, tucking his shirt into his pants before buckling his belt.
“Haha, cucks got a cage on!?” He says loudly in between his laughs. “She’s ready for you, buddy! Can’t believe how tight that cunt is bro. I’m sure I’ll see you again soon!”
As soon as the front door closes behind Jake, I rush to the bedroom and turn the corner. “Oh my god! You’re naked?? I can’t believe Jake just saw you like that!” She said with a touch of nervousness but mostly humor.
I didn’t even acknowledge what she said and went over to her where she was laying on the bed with her legs closed and off to the side, but completely naked. The air in the room felt heavy, almost humid, and it reeked of sweat and sex.
I look to the side of the bed and see a condom, which was relieving, but after closer look I noticed there wasn’t any cum in it. Jessica noticed my realization and said, “So, after all the initial festivities, I had him put the condom on. But they’re your condoms, and I mean, he’s just so big. We used it for a while. I swear we did!! But after a little bit, he said it felt like it was cutting off circulation. And don’t be mad, but I told him he could take it off. And honestly? I wanted him to take it off from the beginning. His cock was too perfect to be using a condom, and when he went in without it it felt soooo good! You’re not mad, are you?”
“No, I’m not mad. But where did he…” I cut off mid-sentence because she spread her legs apart, expecting the question I was in the middle of, and there it was. Jakes cum was leaking out of my wife’s usually perfect and tight, but now gaping slit.
“I had to have his cum in me Michael. When he was about to cum and asked if he should pull out, it was like animal instincts I wrapped my legs around him and held him there for like two whole minutes making sure all of it was in me. It felt so fucking good. I hope you understand?” She said, gauging my response but could tell she wasn’t necessarily sorry.
“Oh my god…” I let it out.
“Hunny!! Please don’t be mad,” she says. Then she looks at my locked cock swelling to the breaking point “oh… You aren’t mad… are you… hot? Does it turn you on?”
“Uhhh,” I let out, embarrassed and not having a quick response because my groin was thinking for me. The entire scene was making me go crazy. I didn’t care another man just came in my wife’s pussy, in some ways I was even happier it happened? I knew this would always be possible if we got into this lifestyle, but I never thought Jessica would go for it, especially not on her first time.
“… do you want to taste it…? That would be hot, you licking his cum from my pussy…. And his cum tasted good, I had no problem swallowing it in the car” she said, now getting excited.
I just sat there staring at her swollen pussy. Completely wrecked and leaking more and more of Jake’s cum out of it as the seconds passed.
“Okay, if you can’t decide, I’ll make it for you. If you want that little cuck dick of yours to be taken out of that cage tonight, then you’ll come over here and lick my pussy until it’s clean!” Jessica said, adamantly now. If there was a chance to get out of it, that chance had passed.
“Uh okay, yes uh yes I will” I was able to mutter out, now climbing closer to her destroyed cunt.
The smell was like something I had never smelt before. It smelt like cum and sex and what not, but it was scents from a different man. It was all different from what I was used to.
“Dig in, it’s not going to clean itself” she said, now staring at me between her legs eyeing up her pussy.
I did as she asked, I took a long lick up her slit. And it was incredible. Something about everything that just happened itched a spot deep inside my soul, and once I started, I couldn’t get enough. I was licking in and around her pussy, fingering her hard to try to get more out. And all of this didn’t go unnoticed.
“Ooohhh, that feels good. You like that, don’t you? You like licking Jake’s cum out of my pussy?” She says with a big smirk on her face as I peek up between her legs and give her a nod before getting back to work. “He came so much hunny, I couldn’t believe it! After he came in my mouth on the drive home I figured there wouldn’t be much, but he came in my pussy two times!! And both of them were huge!! I loved feeling him pulse deep inside of my married pussy.”
All of this dirty talk was making me ravage her mess even more, and she could tell how excited I was.
“Come up here,” she said, motioning me with her finger. “You’ve been a good boy since dinner like I asked, so I’ll hold my end of the bargain.” As she grabs the key and unlocks my cock, allowing it to spring out like a boomerang. “Your turn, but go slow! I’m so sore.”
As I entered her pussy, it was gaped more than I had ever felt it. Which is saying something, because our toys are no joke. It felt so warm and wet. It was like paradise. There was no doubt in my mind that some of Jake’s cum was still inside of her, and my thoughts were confirmed when I pulled out a little more and looked and my little cock was covered in it.
The entire time I’m in her she’s dirty talking in my ear, saying how great everything was and how big and long lasting he was, how much better it felt being full from his cock than mine, how she can’t wait to do it again and how she doesn’t know she’ll ever look at me the same way anymore. It was all getting to me quickly, and in less than a minute, I was about to bust.
Jessica noticed this, and pushed my stomached some to get me out of her “no no no, you are NOT allowed to cum in me. Jake gave very strict rules that he’s the only one allowed to cum in me from now on if I ever want him to fuck me again, and I want him to fuck me again!” She said as I unloaded and had one of the most intense orgasms I’ve ever had, completely covering her chest and stomach with my much-needed load.
“Yeah, good boy. Those balls of yours were probably aching to get that release, huh?” as she patted my balls. “Go grab a towel, clean me up, and get that cage back on before you get any bright ideas.”
I did as she said, cleaned her up with a towel, and begrudgingly locked myself back into my cage.
“You… are something. Tonight was something,” I say to her, basically my first words since we returned to the house.
She blushes and says, “Thank you for putting me up to this. I never knew what I was missing…. Jake should be back in 15 minutes. I told him you wouldn’t last long. I hope you don’t mind sleeping on the couch tonight.”
The End.
*AI has edited this story to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.