want virgin gf to date others

[Daniel97]

Is your brother fucking Jen something you would like to see happen? Have they met?

Or maybe the best would be to just leave it to Jen to choose her next lover herself? I guess the two of you will have some interesting conversations this weekend.

yeah it will be very hot to see Jen with my brother it would be very humiliating especially since he is my younger and is physically superior to me.
and they know each other we are neighbour so he have known jen since we moved to neighbourhood.

For now my plan is to leave the things as it is but i will tell Jen that she is free to date...

 

[irreverent]

Well ... If you talk about dating, and Jen asks you for a suggestion, you could mention your brother? Him being a ladies man, and Jen being a desirable female, I suppose he would be interested, but do you think she would be?

A sexy idea, perhaps, but I agree with you. It's probably best to leave it to Jen to decide on the way forward.

 

[George]

Jen should have lots of choices at her college, especially if she lets people know she likes to fuck. You could get her a 'fuck me' school outfit.
You might find an agressive guy at your school who could keep Jen occupied with him when she is home and otherwise would be having sex with you. Then you could be cucked while she's away and get cucked when she is next door.

 

[midnightfapper]

Jen should have lots of choices at her college, especially if she lets people know she likes to fuck. You could get her a 'fuck me' school outfit.
You might find an agressive guy at your school who could keep Jen occupied with him when she is home and otherwise would be having sex with you. Then you could be cucked while she's away and get cucked when she is next door.

I think this is a good idea, and that the brother is a terrible idea. You want jen to have casual boyfriends/fuck buddies with little to no strings attached. You do NOT want to make a mess of your family with your fetish. Just don't do it. :nono:

 

[George]

Or playing to Jen's playful and submissive sides, you could dare her to wear either nippless bras or no panties each time she meets with or dates a guy until they have sex together.
Or you could dare her to pickup a guy at a frat party (yes, she can walk in without a date) or at a local beer joint, wearing her fuck me outfit.

 

[SquirmingSub]

This would not be the first thread were a girl-friend or wife has taken the boy-friend or husband's brother as a lover. Daniel do you have the foundation to handle the level of humbling humility this could bring about?

 

[Daniel97]

This would not be the first thread were a girl-friend or wife has taken the boy-friend or husband's brother as a lover. Daniel do you have the foundation to handle the level of humbling humility this could bring about?

i feel i can take it as i an already facing humiliation from him as he is more sexual active and taller and stronger than me. Those who have bigger younger brother will know the feeling.

But i dont think Jen will not start a relationship with my brother even if she is sexually attracted to my brother since she have known him since he was kid and babysit him plus he is my brother.

 

[SquirmingSub]

Daniel,

During a prior marriage, while she had slept with many other men (my co-workers, close friends, rivals, her ex-husband to strangers), my than wife always said that she would never be sexual with one of my very close friends (like a younger brother to me) specificity because of what you described in your posted #439 about her baby sat him in the past.

Although the deeper down the cuckold rabbit whole we ventured, the much more adventurous she became and was open to areas in which she had previously considered taboo. This in turn lead to the next time this specific friend made his desires very clear to her, she surprisingly accepted his advances and reciprocated. Was a creative exchange between them.

The next time we were all together she made it crystal clear to me in front of him that he was going to be fucking her any way he wanted that night. After the first session that same night, she told him in front of me how good the sex with him and that he was able to bring her to orgasm quicker through intercourse than I could. She made sure that the experience was a bit humbling and humiliating for me while playing up to his ego at the same time.

So I would say anything is possible if you wanted Jen and your brother to explore a sexual option.

 

[Daniel97]

Daniel,

During a prior marriage, while she had slept with many other men (my co-workers, close friends, rivals, her ex-husband to strangers), my than wife always said that she would never be sexual with one of my very close friends (like a younger brother to me) specificity because of what you described in your posted #439 about her baby sat him in the past.

Although the deeper down the cuckold rabbit whole we ventured, the much more adventurous she became and was open to areas in which she had previously considered taboo. This in turn lead to the next time this specific friend made his desires very clear to her, she surprisingly accepted his advances and reciprocated. Was a creative exchange between them.

The next time we were all together she made it crystal clear to me in front of him that he was going to be fucking her any way he wanted that night. After the first session that same night, she told him in front of me how good the sex with him and that he was able to bring her to orgasm quicker through intercourse than I could. She made sure that the experience was a bit humbling and humiliating for me while playing up to his ego at the same time.

So I would say anything is possible if you wanted Jen and your brother to explore a sexual option.

wow nice share... its always exciting to hear other people experiences...
in our current state i dont thing anything sexual will happen between my brother and Jen, maybe in future something will happen..

 

[SquirmingSub]

Daniel,

As you will find as you get older and if you are successful in this lifestyle you will also have many experiences in the years to come.

 

[irreverent]

Have you talked with Jen about your current status yet? It would be interesting to hear her view of the situation. If she wants to continue cuckolding you and find a new partner, or take a step back and just be your gitlfriend.

 

[SquirmingSub]

Danial and Jen may be all wrapped up in semester finals prep....

 

[Daniel97]

Few days ago Jen met mike the douchebag in our home town. ( Jens exams were one week before mine). He talked with her and told her that she should try new thing and should go with him to club this week as she was alone and getting bored.

Jen talked with me about what he said to her and i told her that she should try going on date with him.

I will be traveling to my hometown tomorrow, lets see what happened on her date with douchebag.

 

[whitney]

Mike fucks Jen , And takes her ass too

 

[SquirmingSub]

Few days ago Jen met mike the douchebag in our home town. ( Jens exams were one week before mine). He talked with her and told her that she should try new thing and should go with him to club this week as she was alone and getting bored.

Jen talked with me about what he said to her and i told her that she should try going on date with him.

I will be traveling to my hometown tomorrow, lets see what happened on her date with douchebag.

This is going to be interesting to hear the outcome.

 

[Daniel97]

Sorry for not updating about Jen date I was too lazy. So Jen have told me all about her date with douchebag. She told me date was better than expected but he was bit of a showoff.

He took her to one of the better club in our city and told her he was friend with the owner so if they want some privacy they can get it but Jen told him no. They drank a little bit but she tried to not drink too much because she does not trust him. He put his hand on her thighs and slowly moved above. He kissed her 3 times each was longer than before and she told me he was very good kisser.

He moved his hand inside her skirt and rubbed her panties and then moved his hand inside her panties but she stopped him because she did not want people to notice. They danced and Mike touched her body on every opportunity he got. She told me she got very wet and her breast and nipples hurt a little because of all excitement.


Afterwards she told him to drop her to her house but he offered if she want to go to his house but she declined. He drove very slowly and it was late at night so there was not much traffic. He showed her the place which he hang out and the tattoo shop that he co-owns. While driving he tried rubbing her but she stopped him. He told her it look like he was not going to get lucky tonight and that’s the fact being guy sometimes you score sometimes you don’t. He told her if she ever wanted a tattoo she can visit his parlor and he can give her special “offer”. ( That’s why I call him douchebag, who talk to girl like that)

Jen told me after reaching home she was very hot and fingered herself. But she don’t think she will go out with him again.
So that’s it for now, it might be not much for many but hearing about it made me orgasm all over my underwear.

 

[Daniel97]

Side note: my brother is dating a black girl. its very humiliating to think that my younger brother have more experience in sex and have fuck 3 girls maybe even popped a cherry. and why do we hear so less about white guy black girl couples.

 

[SquirmingSub]

Daniel,

Great updates. There are times were a girl-friend or wife will have sex with someone that they typically would not date. Have experience in that area were my significant other at the time had sex with a guy that she could not stand because he was arrogant, generally rude yet she was sexual attracted to the guys confidence, in some ways to his arrogance, very much the way he kissed and the way he fucked yet not someone she would have hanged with outside of the sexual meet ups.

 

[powah9845]

nice update! could always get a tattoo that she has to remove clothes for =p

 

[Daniel97]

why is this site so slow nowadays. Very few comments, not many new post posted by people.

Or maybe people have gotten bored with my thread