My girlfriend and my boss
Re: My girlfriend and my boss
Thanks for the update,
I would imagine this kind of meeting will both give you a sense of hope that Isla is coming back to you, but also it could stimulate jealousy I would think. Is that an issue for you?
Sincerely
elina
I would imagine this kind of meeting will both give you a sense of hope that Isla is coming back to you, but also it could stimulate jealousy I would think. Is that an issue for you?
Sincerely
elina
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ShyBiGuy954
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Re: My girlfriend and my boss
newcucktoo wrote: ↑Wed Jul 23, 2025 6:26 amSo Isla and I actually just met for a coffee today. We work near each other, so we met for a quick coffee near our work.
We talked about things. She obviously really likes Peter and is enjoying the sex. “Sooo much” were her words. She did mention that she can’t see him as much now because his wife is back from Europe and he’s been super busy on a work thing. She said she will see him tonight but asked what I was doing on the weekend. I obviously said nothing.
She said she’d heard that Becky and I were having fun and that she was a little jealous. I kind of blurted out that I really missed her and she smiled and said same. She asked if I enjoyed fucking Becky and I said yes of course. But I added it wasn’t the same as her. She smiled.
When it came time to go I asked if I could kiss her. She smiled and we walked up a lane a little off the main street and started kissing. It was a proper I want to fuck you kiss. I felt her breast and she held me close. We kissed for a few minutes and kind of broke off and smiled and she said she’d message me.
I love the way Isla simultaneously insinuates that she's still your Girlfriend but she still teases you that she enjoys fucking Peter.
I'm looking forward to what she has planned for the weekend.
She might be feeling a bit jealous about you with Becky, and that she doesn't want to lose you to Becky.
newcucktoo wrote: ↑Mon Jul 21, 2025 4:11 amLast night Becky decided to get a drink near her house and texted me that she was going to the pub. I was so turned on.
She sent me a photo where she had undone another button or two on her dress and said "too much?". I replied "perfect of you want to get fucked" and she replied "I do"
I was SOOOOOO horny watching those texts and so we are going to meet tonight at my place. I told her to wear that bra tonight.
Care to fill us in on how the visit from Becky went?
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)
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)
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newcucktoo
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Re: My girlfriend and my boss
HI, Sorry it's been a busy week. Becky and I met at a pub straight after work and had a couple of drinks. She said she wanted to chat to some other men in front of me which I didn't mind. She looked so good. So she chatted and flirted and then came back and chatted to me. She's so sexy and was asking me which one she thought wanted to fuck her. I think about five did but there was one guy who was really interested and so she went back and got his number. She then wanted to leave because we were both so horny. We fucked twice! The first time was really frantic because we were both so turned on. She kept talking about the guy and how big his cock was and how she wanted to suck him off and feel him fill her. It was crazy! I have to admit I didn't last very long as I was super excited after talking to you and her last night.
After we chatted she asked me if I would like to eat her pussy and imagine the other guy had just fucked her and so we did that. So I tasted my own cum in her and then she wanted to suck me at the same time so we moved aroudn a bit and she licked my cock as I licked her. Then she wanted to taste my cum on my lips and so kissed fo a bit and then fucked missionary. We both had a great orgasim.
We talked a bit about Isla. She said she spoke to her and she is really good. She is sleeping at his house during the week and he pretends to have to work on Sundays so they have been meeting on Sundays at a luxury hotel. Isla said the sex with him is amazing and she is even doing anal with him which she didn't do with me. Becky said she sounded really happy which is good.
Isla loves how wealthy and powerful he is. He's buying her cothese and shoes. Beck said he likes to dominate her and she's really into that.
Beky actually saw me getting hard again when she was talking about Isla which she commented on.
After we chatted she asked me if I would like to eat her pussy and imagine the other guy had just fucked her and so we did that. So I tasted my own cum in her and then she wanted to suck me at the same time so we moved aroudn a bit and she licked my cock as I licked her. Then she wanted to taste my cum on my lips and so kissed fo a bit and then fucked missionary. We both had a great orgasim.
We talked a bit about Isla. She said she spoke to her and she is really good. She is sleeping at his house during the week and he pretends to have to work on Sundays so they have been meeting on Sundays at a luxury hotel. Isla said the sex with him is amazing and she is even doing anal with him which she didn't do with me. Becky said she sounded really happy which is good.
Isla loves how wealthy and powerful he is. He's buying her cothese and shoes. Beck said he likes to dominate her and she's really into that.
Beky actually saw me getting hard again when she was talking about Isla which she commented on.
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Freemans892
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Re: My girlfriend and my boss
Well this turning into an interesting throuple in sorts.
First off, I’m pretty sure that Peter’s wife knows or knows that Peter has side-chicks. She is either a cuckquean or has her own boyfriend/toy boy/fuck buddy. The indication is that Peter is very dominant and introduced Isla to his friends as his girlfriend. Peter has no concerns about his wife divorcing if she finds out. In fact, Peter knows that newcucktoo danced with his wife when he made the move his girlfriend and is not concerned about newcucktoo saying anything to his wife. I am assuming that Peter is allowed to have a mistress as long as she young enough to be a non-threat to the wife status and is outside their group of friends.
This is good news is sort for newcucktoo because Peter has no intention in replacing his wife. I have read in one case where the where the boss, her boss, got the mistress to dump her fiancé before their wedding. I think Isla is too smart for this to happen.
The damage period for the wife/girlfriend in losing their new cuck is in the NRE phase. This especially the case if the girlfriend or wife goes in hot and heavy with the new lover. The boyfriend/husband feels resentment about being left behind, not always the case but it definitely does happen. This would be definitely be case for a 21 year old male, who has gone fromregular sex to being totally denied by his girlfriend. The pressure release valve solution for Isla = Becky.
My take is that Peter was ready to have the “talk” about the new status going forward with newcucktoo but I reckon that Isla said she will manage it. Isla met with Becky and gave her the full rundown of the situation and the plans going forward. Isla was fully aware of the mutual attraction between newcucktoo and Becky based on previous threesomes together and know Becky would love to have a boyfriend willing to share her. I’m pretty sure that Isla gave Becky full permission before the pub catch-up to be newcucktoo surrogate girlfriend.
Instead of Becky giving newcucktoo the “talk”, she became newcucktoo sounding board and basically started the process of becoming the surrogate girlfriend without newcucktoo realising it. Becky seems just turned on about sharing Isla as you are. Becky also gets turned on with the thoughts of you sharing her. It seems very much like you the exactly the type of guy that Becky wants as a boyfriend.
It wouldn’t surprise if Peter has done this before with his subordinates. Keep an ear and try to find out if Peter has done this before with other male team members in your team. I’m guessing Peter knows he can get away with it as he’s a partner and HR won’t do a thing about it?
I’m also guessing now that Peter has introduced Isla as his girlfriend to his mates, in public, you are now viewed as the ex-boyfriend of Isla? Is this reason why Isla must find a back laneway to kiss you? Is this assumption is correct? What is the go at work events? Are you able to bring Isla?
If I was you, I wouldn’t let Peter know about Becky because the next thing you know is that Peter will be organising a threesome with Isla and Becky. You should also try anal with Becky. In short, what ever Isla does with Peter, you and Becky should replicate. Becky will totally by this and it will keep Isla jealous. I’m pretty sure that Isla and Becky are swapping stories with each other. By keeping Isla jealous, she knows that Peter can’t totally have it all his own way or she may come away as being the loser at all of this. At the moment, things have turned into an interesting throuple.
First off, I’m pretty sure that Peter’s wife knows or knows that Peter has side-chicks. She is either a cuckquean or has her own boyfriend/toy boy/fuck buddy. The indication is that Peter is very dominant and introduced Isla to his friends as his girlfriend. Peter has no concerns about his wife divorcing if she finds out. In fact, Peter knows that newcucktoo danced with his wife when he made the move his girlfriend and is not concerned about newcucktoo saying anything to his wife. I am assuming that Peter is allowed to have a mistress as long as she young enough to be a non-threat to the wife status and is outside their group of friends.
This is good news is sort for newcucktoo because Peter has no intention in replacing his wife. I have read in one case where the where the boss, her boss, got the mistress to dump her fiancé before their wedding. I think Isla is too smart for this to happen.
The damage period for the wife/girlfriend in losing their new cuck is in the NRE phase. This especially the case if the girlfriend or wife goes in hot and heavy with the new lover. The boyfriend/husband feels resentment about being left behind, not always the case but it definitely does happen. This would be definitely be case for a 21 year old male, who has gone fromregular sex to being totally denied by his girlfriend. The pressure release valve solution for Isla = Becky.
My take is that Peter was ready to have the “talk” about the new status going forward with newcucktoo but I reckon that Isla said she will manage it. Isla met with Becky and gave her the full rundown of the situation and the plans going forward. Isla was fully aware of the mutual attraction between newcucktoo and Becky based on previous threesomes together and know Becky would love to have a boyfriend willing to share her. I’m pretty sure that Isla gave Becky full permission before the pub catch-up to be newcucktoo surrogate girlfriend.
Instead of Becky giving newcucktoo the “talk”, she became newcucktoo sounding board and basically started the process of becoming the surrogate girlfriend without newcucktoo realising it. Becky seems just turned on about sharing Isla as you are. Becky also gets turned on with the thoughts of you sharing her. It seems very much like you the exactly the type of guy that Becky wants as a boyfriend.
It wouldn’t surprise if Peter has done this before with his subordinates. Keep an ear and try to find out if Peter has done this before with other male team members in your team. I’m guessing Peter knows he can get away with it as he’s a partner and HR won’t do a thing about it?
I’m also guessing now that Peter has introduced Isla as his girlfriend to his mates, in public, you are now viewed as the ex-boyfriend of Isla? Is this reason why Isla must find a back laneway to kiss you? Is this assumption is correct? What is the go at work events? Are you able to bring Isla?
If I was you, I wouldn’t let Peter know about Becky because the next thing you know is that Peter will be organising a threesome with Isla and Becky. You should also try anal with Becky. In short, what ever Isla does with Peter, you and Becky should replicate. Becky will totally by this and it will keep Isla jealous. I’m pretty sure that Isla and Becky are swapping stories with each other. By keeping Isla jealous, she knows that Peter can’t totally have it all his own way or she may come away as being the loser at all of this. At the moment, things have turned into an interesting throuple.
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newcucktoo
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Re: My girlfriend and my boss
Hi all, so Isla texted to see if we can catch up tomorrow or Saturday night? My question to you all is do you think it is reasonable to ask her if we can have sex before meeting. Yesterday she was horny and said so when we were kissing, especially when I was feeling her breast. I am not sure that she is having as much sex now. any thoughts on what I should do? Thanks,
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BallSpanking
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Re: My girlfriend and my boss
Absolutely! Jump in!
Why would you deny yourself, or her, the opportunity?
Why would you deny yourself, or her, the opportunity?
Schwiiiiing ... Thud! (Projectile erection becomes vicious uppercut KO!)
Re: My girlfriend and my boss
Well,
You can ask, but I don't think you want to make sex a condition for meeting with Isla.
If She doesn't want to let you fuck Her, maybe you can ask to lick Her pussy, it is a good way for a cuck to reconnect with their Cuckoldress.
You can ask, but I don't think you want to make sex a condition for meeting with Isla.
If She doesn't want to let you fuck Her, maybe you can ask to lick Her pussy, it is a good way for a cuck to reconnect with their Cuckoldress.
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ShyBiGuy954
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Re: My girlfriend and my boss
Yeah, I wouldn't make sex a condition for meeting.
I think the meeting should be more about how you miss each other, and a reinforcement/confirmation that she still considers you two as a couple, aka BF and GF, and she's just loaning her body out to Peter 'cause she likes to fuck him.
I'm sure she's subconsciously thinking if she doesn't reconnect with you soon she will lose you to Becky.
.
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)
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)
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newcucktoo
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Re: My girlfriend and my boss
Ok, so I texted her and said "so are we allowed to have sex?"
and in true Isla style she said "we're adults we can do what we want. Do you want to"
and in true Isla style she said "we're adults we can do what we want. Do you want to"
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BallSpanking
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Re: My girlfriend and my boss
Did you immediately respond with a 'yes'?
Schwiiiiing ... Thud! (Projectile erection becomes vicious uppercut KO!)
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newcucktoo
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Re: My girlfriend and my boss
Yes of course
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ShyBiGuy954
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Re: My girlfriend and my boss
Did you ask her about Peter's request last week, when she was at your house sitting on your lap, that he did not want her having sex with you ?newcucktoo wrote: ↑Thu Jul 24, 2025 10:51 amOk, so I texted her and said "so are we allowed to have sex?"
and in true Isla style she said "we're adults we can do what we want. Do you want to"
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)
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)
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newcucktoo
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Re: My girlfriend and my boss
No I thought best not to mention it. Maybe she's forgotten. I got the impression yesterday that she's not having as much sex now his wife is back
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ShyBiGuy954
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Re: My girlfriend and my boss
You better bring your "A" game, LOLnewcucktoo wrote: ↑Thu Jul 24, 2025 11:25 amI got the impression yesterday that she's not having as much sex now his wife is back
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)
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)
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Freemans892
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Re: My girlfriend and my boss
I love the latest updates. Hopefully it means that you and Isla will be able to reconnect on a more regular and sustainable basis. As a 21 year old working for a partner as a boss, I expect you have a heavy workload during the week and need to work long hours and thus haven’t always been available on week nights for Isla. I also expect that Peter is expected to be the family man on the weekends and his wife wants him around. With the wife back town from holidays, the wife takes priority over the mistress thus Isla daily sex with Peter has dried up to probably only 2 to 3 times a week. I expect things will become more manageable going forward in getting quality time with Isla.
As for Becky, keep on having dates with her. It seems you and her have been having a lot of fun with the process of sharing her with other men and encouraging her to give out her phone number with other men, then having hot sex afterwards. Also with Becky, you able to recreate scenarios that Peter has done with Isla in bed and be dominant. I suspect that both Becky and Isla can be quite submissive in bed, Isla enjoys Peter being dominant and Becky enjoys you being dominant. I also suspect that Isla actually gets turned on about hearing what you and Becky get up to on your dates together and admires you when you play the stag role with Becky. A win-win situation. I’m suspecting that you enjoy being a cuck and a stag and Isla enjoys being a Hot Girlfriend/Hotwife and a cuckquean, all at the same time.
Good luck with reconnecting with Isla on the weekend.
As for Becky, keep on having dates with her. It seems you and her have been having a lot of fun with the process of sharing her with other men and encouraging her to give out her phone number with other men, then having hot sex afterwards. Also with Becky, you able to recreate scenarios that Peter has done with Isla in bed and be dominant. I suspect that both Becky and Isla can be quite submissive in bed, Isla enjoys Peter being dominant and Becky enjoys you being dominant. I also suspect that Isla actually gets turned on about hearing what you and Becky get up to on your dates together and admires you when you play the stag role with Becky. A win-win situation. I’m suspecting that you enjoy being a cuck and a stag and Isla enjoys being a Hot Girlfriend/Hotwife and a cuckquean, all at the same time.
Good luck with reconnecting with Isla on the weekend.
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scarfolamew
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Re: My girlfriend and my boss
This is so fucking hot. Girls are just flocking to you to fuck you and cuckold you. A cuck with a goddamn harem, I can't even
My story: viewtopic.php?f=8&t=73151
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newcucktoo
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Re: My girlfriend and my boss
O so Isla is staying at my place tonight. She said Peter is gogin back to his country house and his wife is back. He won't be back until Sunday night. She's gogin to meet him Sunday afternoon
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newcucktoo
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Re: My girlfriend and my boss
I thought you be interested in how my night with Isla went.
She came over after work last night and I decide to cook her dinner. I cooked her favourite pasta which is pretty simple. She thought that was beautiful. Even before she knew about dinner we shared a nice kiss at the door and I told her how much i'd missed her. She looked amazing. We talked and laughed as I finished cooking and enjoyed some wine and some yummy food together. After dinner Isla suggested we watch Netflix and so went to get changed. She came out in one of my t shirts and undies.
We settled in to watch Netflix and it didnt take long for us to start making out and me fingering me. She suggested we go to bed and we kind of ran to bed. Was fun. We stripped and I started licking her and she wanted my cock in her mouth so we 69ed for a bit and then she just said I need your cock inside me and so I got on top.
Just before I pushed inside her she said "you should wear a condom" and so we found one and she put it on. I was kind of expecting that so wasn't worried. We fucked and kissed missionary. She was very vocal and horny and we came. Was so good.
We were kissing and chatting and my cock was still inside her and I said I felt like I was reclaiming her and she said she liked that. After a little bit we cleaned up and got back into bed and I think we were both asleed within 10 minutes. It's been a full on week. We slept naked and it felt so good to be next to her again.
About 2 or 3 in the morning she was kissing my face and neck and when I woke she asked if I was awake. I said I was now. She started kissing me and it didn't take long for me to get hard and she pulled me on top of her and just said fuck me. I said I need a condom and she said no. I need to feel you inside me and so we fucked. It was a bit rough and full on and she told me to cum in her and reclaim her c***t and so i did. Was so amazing. We fell asleeep.
I woke and she was in the shower and suggested we go out for breakfast and so we showered and walked down the street. We held hands and it was like Peter and Becky never existed.
During breakfast she was a little quiet. When I asked if she was ok, she said I don't think I should have done that. I said what and she said fucked without a condom. I'm Peter's girlfriend. I said I wonldn't tell but she said she shouldn't. After a little while I said why can't you have two biyfriends. And she was surprised by the idea. Peter and you she said? I said why not.
She did ask how Becky was and I explained what happend. She said she thought that was hot and was quite interested. She said I should still see her. She said she knows Becky wants to.
She is meeting Peter tomorrow at a fancy hotel and so she wanted to get organised to see him.
I invited her home but she said she had stuff to do and so we just kissed at my place when we picked up her stuff and she went home.
About 30 minutes after she left Becky texted to catch up.
She came over after work last night and I decide to cook her dinner. I cooked her favourite pasta which is pretty simple. She thought that was beautiful. Even before she knew about dinner we shared a nice kiss at the door and I told her how much i'd missed her. She looked amazing. We talked and laughed as I finished cooking and enjoyed some wine and some yummy food together. After dinner Isla suggested we watch Netflix and so went to get changed. She came out in one of my t shirts and undies.
We settled in to watch Netflix and it didnt take long for us to start making out and me fingering me. She suggested we go to bed and we kind of ran to bed. Was fun. We stripped and I started licking her and she wanted my cock in her mouth so we 69ed for a bit and then she just said I need your cock inside me and so I got on top.
Just before I pushed inside her she said "you should wear a condom" and so we found one and she put it on. I was kind of expecting that so wasn't worried. We fucked and kissed missionary. She was very vocal and horny and we came. Was so good.
We were kissing and chatting and my cock was still inside her and I said I felt like I was reclaiming her and she said she liked that. After a little bit we cleaned up and got back into bed and I think we were both asleed within 10 minutes. It's been a full on week. We slept naked and it felt so good to be next to her again.
About 2 or 3 in the morning she was kissing my face and neck and when I woke she asked if I was awake. I said I was now. She started kissing me and it didn't take long for me to get hard and she pulled me on top of her and just said fuck me. I said I need a condom and she said no. I need to feel you inside me and so we fucked. It was a bit rough and full on and she told me to cum in her and reclaim her c***t and so i did. Was so amazing. We fell asleeep.
I woke and she was in the shower and suggested we go out for breakfast and so we showered and walked down the street. We held hands and it was like Peter and Becky never existed.
During breakfast she was a little quiet. When I asked if she was ok, she said I don't think I should have done that. I said what and she said fucked without a condom. I'm Peter's girlfriend. I said I wonldn't tell but she said she shouldn't. After a little while I said why can't you have two biyfriends. And she was surprised by the idea. Peter and you she said? I said why not.
She did ask how Becky was and I explained what happend. She said she thought that was hot and was quite interested. She said I should still see her. She said she knows Becky wants to.
She is meeting Peter tomorrow at a fancy hotel and so she wanted to get organised to see him.
I invited her home but she said she had stuff to do and so we just kissed at my place when we picked up her stuff and she went home.
About 30 minutes after she left Becky texted to catch up.
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ShyBiGuy954
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Re: My girlfriend and my boss
Well, under those terms you've just flipped the script. You just fucked Peter's girlfriend, LOLnewcucktoo wrote: ↑Sat Jul 26, 2025 12:17 pm
During breakfast she was a little quiet. When I asked if she was ok, she said I don't think I should have done that. I said what and she said fucked without a condom. I'm Peter's girlfriend.
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)
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)
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newcucktoo
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Re: My girlfriend and my boss
lol. Yes I didn’t think about it like that. Lol.
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Cuckcuckgoose1
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Re: My girlfriend and my boss
I'm still trying to wrap my mind around what "me fingering me" means....
Lol
Lol
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Freemans892
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Re: My girlfriend and my boss
In the interim, you have become Isla’s Bull and Isla had indicated that she wants you and Becky to become boyfriend and girlfriend. Becky has already given permission on behalf of Isla and herself that you can have side-chicks. You can a hell of a lot of fun with this scenario.
Isla has basically admitted she’s a bit of a cuckquean, and Becky is probably is too. I see interesting adventures ahead exploring your kicks.
Are Isla and Becky bisexual?
Isla has basically admitted she’s a bit of a cuckquean, and Becky is probably is too. I see interesting adventures ahead exploring your kicks.
Are Isla and Becky bisexual?
Last edited by Freemans892 on Sat Jul 26, 2025 6:14 pm, edited 2 times in total.
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ShyBiGuy954
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Re: My girlfriend and my boss
In terms of Becky and the guys she's been flirting with lately. The guy that was touchy/feely while she was playing pool at the pub, and the guy she got his number when you two went out the other night, Do you think she has plans to actually date/fuck these guys, or do you think she is just flirting because she knows you like it, and you both get turned on enough to go home and fuck?
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)
Me: Of course, why?
Her: Your my second date tonight, I already fucked ******
(it was a guy I worked with)
Re: My girlfriend and my boss
I imagine that's supposed to be "me fingering her".Cuckcuckgoose1 wrote: ↑Sat Jul 26, 2025 2:43 pmI'm still trying to wrap my mind around what "me fingering me" means....
Lol
Re: My girlfriend and my boss
WOW, what an adventure. Thank you so much for sharing. I like how hard you get knowing that Isla is getting fucked by Peter when Becky tells you that.. and that you always get hard when Becky is flirting and having fun with others... You are having such a good time... Really hot that Isla woke you up to fuck too.. WOW... Thanks for sharing and looking forward to the updates... Best of luck