My girlfriend and my boss

For cuckoldresses and the men who serve them.
Cuckcuckgoose1
Pervert
Posts: 521
Joined: Tue Feb 20, 2024 3:07 pm

Re: My girlfriend and my boss

Unread post by Cuckcuckgoose1 » Fri Jul 11, 2025 3:38 pm

Oh you just conveniently left that part out huh?

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Fri Jul 11, 2025 3:57 pm

I apologize. I didn't mean to leave it out. It's just hard to include everything without writing massive posts and I didn't want to bore you. So there's probably bits missing. But it's not intentional.

User avatar
leggysman
2 Bit Whore
Posts: 1427
Joined: Wed Feb 22, 2023 10:46 pm
Location: UK

Re: My girlfriend and my boss

Unread post by leggysman » Fri Jul 11, 2025 5:30 pm

newcucktoo wrote:
Fri Jul 11, 2025 3:57 pm
It's just hard to include everything without writing massive posts and I didn't want to bore you.
That your girlfriend fondled your boss's cock and balls, seems highly unlikely to be a detail that's going to 'bore' your readers here.
our hotwife story: viewtopic.php?f=5&t=67232
leggysandy's pics: viewtopic.php?f=9&t=67265

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Fri Jul 11, 2025 5:45 pm

Lol. That's true. ok. So remember this isn't the first time they have met. So when they were dancing downstairs he was whispering how much he wanted her and she could feel that his cock was hard against her. She said that he would kiss her ears and neck while they danced and she wanted him. So they went to a smaller room and were kissing and he wanted her to suck him off but she was so horny she wanted sex but realized they couldn't but he convinced her to hold his cock. She said that he's bigger and thicker than me and his balls very full of cum.

Later in the night she was talking with his wife and she said last night that he must be so fertile because he has three kids and she wants his cum to flood her womb. We sometimes play with unprotected sex.

venus-can99
OHW Addict
Posts: 3093
Joined: Thu May 25, 2023 11:57 am
Location: Not the 51st State

Re: My girlfriend and my boss

Unread post by venus-can99 » Fri Jul 11, 2025 8:31 pm

Breeding fantasies and unprotected sex can be fun to imagine but I am sure you and gf are pretty smart about the practical aspects of unprotected sex play.
Hope both of you have fun - she getting filled by a bigger and thicker cock - and you seeing your wonderful sexy gf filled
Last edited by venus-can99 on Sat Jul 12, 2025 2:11 pm, edited 2 times in total.

troilusand
Pervert
Posts: 527
Joined: Wed Apr 29, 2009 8:48 pm

Re: My girlfriend and my boss

Unread post by troilusand » Sat Jul 12, 2025 11:09 am

Cuckcuckgoose1 wrote:
Fri Jul 11, 2025 1:07 pm
"Trust, but verify".
I like my catfish with Tobasco...

Troilus
For a glimpse at our history, see...25th Anniv. of Troilus and Cressida in the Library...non-fiction!

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Sat Jul 12, 2025 6:47 pm

OK. I don't really understand

oldboy
Virgin
Posts: 24
Joined: Sun Sep 11, 2022 10:05 pm

Re: My girlfriend and my boss

Unread post by oldboy » Sun Jul 13, 2025 5:33 am

One of the Best threads

oldboy
Virgin
Posts: 24
Joined: Sun Sep 11, 2022 10:05 pm

Re: My girlfriend and my boss

Unread post by oldboy » Sun Jul 13, 2025 5:34 am

One of the Best threads

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Mon Jul 14, 2025 5:40 am

Hi, So I found out on the weekend that Isla has already been fucking Peter.

I feel a bit embarrassed to say this because although I had a gut feel that was the case, I didn't know for sure. She would often drop little hints but she told me everything (I think everything) this weekend. I'll post it her over a few posts as it's long and I'm still trying to get my head around it.

So it started a few weeks ago at a BBQ/pool party at Peter's house in the country. He has a big house and had some friends and work people over. It was a hot day and so we were all in and out of the pool and the drinks flowed. Isla was wearing a small light blue bikini and she and Peter spent lots of time in the pool together. You could see her nipples and he was very interested in her. She was also very attracted to him. They were laughing and playing games in the pool for ages.

Evidently, later in the day she asked him where the toilet was and he showed her inside but instead of going to the one downstairs he showed her to the one off his bedroom. She said he showed her around his bedroom and his bed and said she was welcome in it anytime.

She said it was clear he wanted to fuck her.

She didn't know what to do so she went to the loo and he stayed in his room talking to her. She said she was super horny and so she decided to come out of the loo into his room naked. So she took off her bikini and walked into his room.

She said they kissed of a while and then she sucked him off. He held her head and fucked her mouth which she loved. She wanted him to fuck her but they knew they didn't have much time so she swallowed his cum and then they got dressed and came back to the pool. So that's how it started with him.

venus-can99
OHW Addict
Posts: 3093
Joined: Thu May 25, 2023 11:57 am
Location: Not the 51st State

Re: My girlfriend and my boss

Unread post by venus-can99 » Mon Jul 14, 2025 5:59 am

Wow! How did you feel when she confessed to this? How did she feel? And your relationship do you think it is still on solid ground? Would you be ok if she continues her affair with Peter? So many questions...But I will wait for your retelling

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Mon Jul 14, 2025 6:16 am

Hi, I feel a bit confused to be honest. As I said, I thought she probably was fucking him but wasn't sure and certainly didn't know how much. I'm actually not sure about our relationship now. We don't live together and so I haven't seen her since Friday but we're catching up tonight so I should know more tonight I guess.

So Maybe I'll keep going. I was worried you would all laugh at me so hopefully that doesn't happen.

So the bbq went on through the night. And LOTS of drinks flowed. Isla said she even ripped the lining from her bikini when they decided to get into the spa. She ended up sitting on Peters knee in the spa as it was crowded. I left the spa and went inside and fell asleep on the couch as I'd had lots to drink. She told me that he fingered her in the spa when I was in there and she opened her legs for him to make it easier.

As everyone drifted off, Peter and Isla went into the bedroom in the guest cottage near the pool. She said it didn't take long for him to start fucking her. she said she wanted missionary so she could open herself for him and feel him close to her. She said she loves his chest hair as it's so manly and primal. She said he kissed her when he came inside her which she loved. They used a condom.

After a bit they came inside and she got me and we got a uber and he went back to his wife.

So that was the first time. As I said I knew about the flirting and touching, even in the spa but I didn't know the rest.

venus-can99
OHW Addict
Posts: 3093
Joined: Thu May 25, 2023 11:57 am
Location: Not the 51st State

Re: My girlfriend and my boss

Unread post by venus-can99 » Mon Jul 14, 2025 6:32 am

IMO having a sincere conversation would help - not just about fucking Peter but how she sees your role in the relationship, how the 2 of you feel and so on...

elina
OHW Addict
Posts: 1997
Joined: Sun Mar 05, 2023 1:29 am

Re: My girlfriend and my boss

Unread post by elina » Mon Jul 14, 2025 6:37 am

Well,

Congratulations Newcucktoo

You did secretly want this to happen didn't you?

You now know you have a very sexy, attractive Girlfriend who has no qualms about cucking you....

Looking forward to seeing more updates.
Does your Girlfriend intend to continue fucking your boss? It seems that She really likes it.

Sincerely
elina

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Mon Jul 14, 2025 6:43 am

venus-can99 wrote:
Mon Jul 14, 2025 6:32 am
IMO having a sincere conversation would help - not just about fucking Peter but how she sees your role in the relationship, how the 2 of you feel and so on...
Hi Yes I agree. I think that's what I need to understand better. What she wants and how I fit into that. I guess I am just a little confused about the options. Thanks

Vin231
Pervert
Posts: 608
Joined: Wed Mar 20, 2024 10:47 am

Re: My girlfriend and my boss

Unread post by Vin231 » Mon Jul 14, 2025 6:44 am

Sounds like things are moving fast and I do hope for the Best for you both. I do love that you are wanting Isla to fuck your boss and it seems like she likes the idea as well. Great role play too to spice up the sex. Didn't realize that the Peter and Isla got so intimate at the party. Has Peter asked you for photos of Ilsa yet? I bet she would love posing for him. Might be a fun game too. I would love to see Isla, maybe post her on the Hotties forum.

looking forward to your next update and enjoy the ride. Best of luck

Vin231
Pervert
Posts: 608
Joined: Wed Mar 20, 2024 10:47 am

Re: My girlfriend and my boss

Unread post by Vin231 » Mon Jul 14, 2025 6:45 am

Sounds like things are moving fast and I do hope for the Best for you both. I do love that you are wanting Isla to fuck your boss and it seems like she likes the idea as well. Great role play too to spice up the sex. Didn't realize that the Peter and Isla got so intimate at the party. Has Peter asked you for photos of Ilsa yet? I bet she would love posing for him. Might be a fun game too. I would love to see Isla, maybe post her on the Hotties forum.

looking forward to your next update and enjoy the ride. Best of luck

njcouplenj
Trainable
Posts: 52
Joined: Mon Feb 25, 2019 9:20 am

Re: My girlfriend and my boss

Unread post by njcouplenj » Mon Jul 14, 2025 6:48 am

It sounds like you’re still processing everything, especially now that Isla confirmed she’s been with Peter:
  • How did it feel when Isla finally confirmed she’d been fucking Peter? Was it a shock or more of a confirmation of what you already felt? Did the erotic excitement outweigh the surprise or jealousy
  • Has your dynamic with Isla changed since this came out? Are you still fantasizing about her with other men, or are you re-evaluating how far you want to take this?
  • How do you feel about Peter now? Do you see him as a threat, a turn-on, or something in between?
  • Is Isla still seeing him, or has she said anything about continuing that relationship? Would you be okay with that if she wanted it to become more regular?
  • Have you two talked about boundaries yet? Now that the fantasy is real, it might be time to discuss what feels good, what doesn’t, and what you want out of this going forward.

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Mon Jul 14, 2025 7:24 am

njcouplenj wrote:
Mon Jul 14, 2025 6:48 am
It sounds like you’re still processing everything, especially now that Isla confirmed she’s been with Peter:
  • How did it feel when Isla finally confirmed she’d been fucking Peter? Was it a shock or more of a confirmation of what you already felt? Did the erotic excitement outweigh the surprise or jealousy
  • Has your dynamic with Isla changed since this came out? Are you still fantasizing about her with other men, or are you re-evaluating how far you want to take this?
  • How do you feel about Peter now? Do you see him as a threat, a turn-on, or something in between?
  • Is Isla still seeing him, or has she said anything about continuing that relationship? Would you be okay with that if she wanted it to become more regular?
  • Have you two talked about boundaries yet? Now that the fantasy is real, it might be time to discuss what feels good, what doesn’t, and what you want out of this going forward.

Yes, I'm still processing but things seem a bit better. We have been texting today and everything seems normal. So your questions....

1) I guess I wasn't shocked that she was fucking him as I suspected that and she had dropped lots of hints, it was more how their relationship has developed and become romantic and caring. And the way she talks about him like he's her partner and she adores him.

I'll skip forward a few weeks but last night they spent the night together at an expensive hotel and he bought her some expensive shoes yesterday. And she said she loved making love to him in the morning as the sun came up and knowing she had had his cock today and she can walk around all day with that feeling.

It's things like that I', not sure how to process yet.

Oh they have stopped using a condom now she warned me. I think his sperm is a turn on for her.

I'll come back to your other questions later if that's ok

ShyBiGuy954
Player
Posts: 418
Joined: Thu Dec 09, 2010 1:48 pm

Re: My girlfriend and my boss

Unread post by ShyBiGuy954 » Mon Jul 14, 2025 8:07 am

newcucktoo wrote:
Mon Jul 14, 2025 7:24 am

I'll skip forward a few weeks but last night they spent the night together at an expensive hotel and he bought her some expensive shoes yesterday. And she said she loved making love to him in the morning as the sun came up and knowing she had had his cock today and she can walk around all day with that feeling.
Ahhh, I wasn't expecting that. I thought you had been describing most of this in real time, not something that happened weeks ago and now has become a regular thing for them.

At this point does your Boss know that you are aware, or does he still think she's cheating on you and you are the clueless boyfriend to her escapades?

And, since Isla's told you this much info about her activities and you haven't balked, she knows that you are at least OK with it for now, and that maybe it even turns you on a bit. Especially now that you've turned the corner from being cheated on, to aware of them fucking, and you're now an accepting your new cuck status.
.
Her: Did you like eating my pussy tonight?
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)

BallSpanking
OHW Addict
Posts: 7457
Joined: Tue Sep 11, 2007 4:58 pm

Re: My girlfriend and my boss

Unread post by BallSpanking » Tue Jul 15, 2025 9:09 am

Sounds like she is bonding with her new BF, and she will be full of NRE ... But will he be willing to share her too?
Schwiiiiing ... Thud! (Projectile erection becomes vicious uppercut KO!)

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Tue Jul 15, 2025 9:23 am

Hi All,

We caught up last night which was really good. She came over and we started kissing as soon as she came in. I was so turned on but as I started to undress her she suggested we sit on the couch and talk. I sat down and she straddled me. My cock was hard. We then talked through everything including their date yesterday. He picked her up ad they went to a fancy hotel in the city. She said they fucked as soon as they got into the hotel and then they went shopping. He bought her a dress and some expensive shoes. He introduced her to people as his girlfriend and held hands while walking. She said she felt so special and proud to be holding his hand. She loved kissing in the park. She said he is so mature and romantic. She said when they got back to the hotel they made love and they have stopped using condoms. She was pleased to have his cum inside of her. Evidently they had a bath and then fucked again before sleeping the night together.

She told me all this and I came in my pants. She just smiled. I noticed she had a bite mark on her breast. After I came she was pretty quick in saying she had to go but wanted to catch up in the week. She warned me that she was Peter's girlfriend now so I'm not sure what that means.

wannabecUKold
Pervert
Posts: 695
Joined: Thu Feb 23, 2023 1:51 am

Re: My girlfriend and my boss

Unread post by wannabecUKold » Tue Jul 15, 2025 9:58 am

It means she’s not yours any longer. But since he’s married she is his mistress not his girlfriend: jewels, trips away, fancy hotels but not Christmas.

newcucktoo
Experienced
Posts: 103
Joined: Tue Jul 08, 2025 5:05 am

Re: My girlfriend and my boss

Unread post by newcucktoo » Tue Jul 15, 2025 10:00 am

That's what I am worried about. Im not sure what to do

ShyBiGuy954
Player
Posts: 418
Joined: Thu Dec 09, 2010 1:48 pm

Re: My girlfriend and my boss

Unread post by ShyBiGuy954 » Tue Jul 15, 2025 10:07 am

newcucktoo wrote:
Tue Jul 15, 2025 10:00 am
That's what I am worried about. Im not sure what to do
Right now just wait. See what she comes back with later in the week when you meet up again. She's probably still trying to figure out what she wants since this is all so new to her too.

Also, he may be guiding her a bit in how he wants her to deal with you.
Her: Did you like eating my pussy tonight?
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)

Post Reply