want virgin gf to date others

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Daniel97 said:
Today I had a long talk with jen about dating others

Jen told me aaron sat with her during two classes and they talked a lot. He asked her if she has a bf she told him yes but didn’t mentioned that I m her bf. They talked some more about their hobbies etc and he asked if he can drop her to her home after college, she was bit reluctant at first but agreed as its getting colder in evening. They also talked about his ex gf and jen told me she sounded like bitch to break up 1.5 year of relationship without even giving long distance relationship a chance ( I don’t know if aaron or his gf was the one who initiated break up but I think it was mutual ). I asked her what she think about aaron, she told aaron a nice and friendly guy but knowing he was hitting on her and have a crush on her make it bit embarrassing for her. I asked her if he was boyfriend material, she said while laughing that he was he is handsome, tall ( I am not) and have a car (I don’t even have license). I told her maybe she should date him she did not reply for few minutes I asked her what happened. She told me I have been acting weird last few days I said that ever since we were teen we have been dating and maybe she should date other before we take next step. She asked me if I wanted to breakup, I told her no I don’t want to but I want her to date some other guy before we decide where to go with our relationship. She asked what about me how will I feel, I told her its ok that why I brought this up. She asked what about me dating a girl, I asked if she wanted me to date others girls, she replied “no”. I told her she should try dating aaron as he is nice guy and have crush on her. She told me she did not want to date, I told her to think about it for sometime and then give answer and I would be happy if she say yes. She gave me a wear ok and said she will think about it.

sorry for one long paragraph

I like this post as it gives a lot of information for us readers. If she dates Aaron or someone else, gosh anything could happen. :):):love::love::clap: I really admire you for being so brave to tell her your thoughts.
 
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i am going to jen’s room to hang out and get her reply if she is willing to date others, will try persuade her to agree.
wish me luck.
 
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Good luck! Let us know how it goes!
 
While hanging out with jen I asked her of she have given any though to the idea on dating others guys. She told me she have been thinking about it but does not understand why I want her to date others she asked if was some kind of test. i assured her it was not any kind of test.

I told her I desire to see her date others and I have been thinking about it a lot. I told her I want her to enjoy her college life. I don’t want her to slow down her life because of me, and find it excited that others guys are attracted to her and if she dates. She told me that all this was too weird. I asked her if she read the article I sent to her about cucking and told me she have, she find it weird that a guy wants other guys to have woman he loves. I told her it was more common that she thinks.

I told her to give it a trial run of 1 month and date aaron as he already like her. She told me she does nit want to play with aaron feelings. I told her if she want some other guy she can date him instead of aaron she gave me same answer she don’t want to play with others feeling. I begged and tried to make her agree for almost an hour and she agreed weakly to try it.

I told her she should go on a small lunch date with aaron tomorrow. She agreed to it but was not able to sent msg she was too nervous so I took her phone and message aaron if he wanted to meet for lunch tomorrow. Within seconds aaron called jen, she talked to him and made plan to eat together. They talked for next 5 mins then they hang up the phone. I asked her how did it went, she replied that I have heard everything, I said that I didn’t heard his side of conversation she told me they planed where they will go and aaron asked if they can hand out later after lunch and jen agreed.

Jen told me she does not feel right deceiving aaron like that, I told her she is mot deceiving aaron and aaron wanted to date her and she should be her true self with aaron and enjoy herself and don’t think about me only give your attention to aaron during date that way she wont feel bad. She stared at me like I have grown horn and asked if I have been rehearsing that speech for a long time. It kindof broke the tension in the room and then jen asked if I was still 100% sure, I nodded. She told me nothing will happen between then and after 1 month I should go back to being me and not bring this up again.

I told her if she is already made her mind that this trail thing will fail and told her to open her mind and heath and enjoy the dates. I made her promise that she wont think about the me or that this is trial period and she will enjoy her date with aaron as much as possible. Afterwards we ordered pizza and talked about others thing instead of my fantasy and then we hugged but did not kiss :( and I left for my room.

Lets see what will happen tomorrow. Was I too pushy?
 
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i want to let people know that Jen losing her virginity to other guy is a part of my fantasy thats why i have not tired to make any progress sexually.
 
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You have pushed hard, and Jen is clearly worried about deceiving Aaron. At some stage, Aaron will ask her what her boyfriend's name is, and Aaron will get a shock to find out it is you.

I think Aaron will make the most of dating Jen, because he is lonely from breaking up with his girlfriend after 18 months.

Aaron and Jen could grow their friendship a long way in a month, and when the "trial is over", they both might find it hard to suddenly stop seeing each other. Getting Jen to add an extra month to the Trial may not be very difficult if she has enjoyed Aaron's friendship.

Aaron will kiss her at the first opportunity, and she won't get any warning of it happening. It will stir up her emotions, and, you need to remember that Aaron has a car licence, and Jen volunteered that Aaron is tall and handsome.

You might be playing with a box of matches.

Not telling Aaron about you and Jen being in love with each other, is a tricky situation.

At the moment, you are the Default Boyfriend that Jen has always knocked around with - but anything may happen when Jen learns to feel good about loving several men at a time.
 
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Daniel97 said:
i want to let people know that Jen losing her virginity to other guy is a part of my fantasy thats why i have not tired to make any progress sexually.

Jen may keep his baby and marry him if contraception fails. I guess you have thought of this significant possibility.
 
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Saraha said:
Jen may keep his baby and marry him if contraception fails. I guess you have thought of this significant possibility.

hi Sahara its bit too early to be thinking about jen being pregnant i haven't thought of that possibility, Contraception have very low chance of failing and i am sure Jen would be extra careful because her mother also become pregnant at early age therefore jen must know the risk.
 
Daniel97 said:
Lets see what will happen tomorrow. Was I too pushy?

I think you did pretty well. It's can be surprisingly difficult to bare your soul to someone who's close to you, and you deserve congratulations for continuing to be honest and communicative with Jen.

Something that I would add is that you should emphasize how this is something that the two of you can play with together. Ideally, the message is not 'Please date Aaron and forget about me', and more to the effect of 'It would be really hot for both of us if you play around like this'. Emphasize that you're not trying to push Jen away; you're trying to set up a game that you can both play, and enjoy together.

If I were you, I'd stress to your GF that you're not trying to undermine your relationship; if anything, you're more committed to her than ever before. What you want to do is give her the freedom to 'take a walk on the wild side'. If she doesn't want to exercise that option, that's up to her, and you'll support her in that decision. But if she does want to play around like this, she can do so knowing that you'll remained devoted to her throughout.

As part of this, I think that you should pay close attention when she raises concerns about 'playing' with Aaron's feelings. This might be an excellent juncture to sound out on what each of you are comfortable with right now, and perhaps discuss what sort of limits should be placed on the play right now. Nothing's written in stone; you can always come back and renegotiate things later if your dynamic changes in the future. For now, though you might want to, as a pair, lay down some limits on how far things should progress to maintain your mutual peace of mind.

Do a lot of listening. Ask her how to explain how she feels about all this, and listen carefully to what she says. You should take careful account of what her concerns might be, what she is and isn't open to, and whether there's something in particular that interests her, that you could potentially expand on.

Another thing you might consider introducing, although this definitely depends on your interests and mutual comfort levels, is tease-and-denial or chastity play. I don't know how sexually comfortable the two of you are; obviously, if your relationship isn't intimate to this level, it's not really an option (and coming home with a chastity cage all of a sudden might be a bit much at this point). If you are comfortable with it, though, tease-and-denial or chastity are good ways to for a couple to remain intimate and connected without engaging in penetrative sex.

Thanks for continuing to share; here's hoping you hear good things about Jen and Aaron's meet-up.
 
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Jen is on her date with aaron and I have masturbated multiple times in last last hour thinking about jen on her date with aaron.
since its their first date if you call it a date, nothing will happen yet just thinking about them is too much for me.
 
Daniel – it takes time for women to process this type of lifestyle. Some take to it like a fish to water and others will not. You should not push Jen to hard, make it clear what your fantasy is and make sure that she understands that you are not testing her or using this as an excuse to date other women. You have also mentioned that Jen does not want to hurt the feelings of another guy such as Aaron. It is good to Jen asked to you to make sure that you are still 100% sure that you wanted her to date another guy, she will likely ask you on multiple occasions as you both take this journey together. It is good that Jen listened to what you had to say and she is given your fantasy some consideration and at the least she is going on a lunch date with Aaron with your encouragement. Jen needs to understand that this is something that you and she are doing together and you are not trying to push her away.

So that I clearly understand, you have not attempted to move your relationship with Jen from a soft sexual (generally platonic) status into fully sexual relationship as you do not want to be man that she loses her virginity to. Your fantasy is about Jen dating others with the primary goal of Jen losing her virginity to another man which could very well be Aaron. It is one thing for your girl friend or wife enjoy another man sexually, it is at a much deeper level if you are truly encouraging her to give up her virginity to another man, something that many man would like to have. Make sure this is truly want you desire and if it is than Jen needs to know that you will continue to encourage and support her in this journey. As you have told Jen, she should not be thinking about you while she is on a date with another man and she should not be worried about deceiving Aaron, Aaron knows up front that she has a boy friend going into the first date. While this may be a trial period of one (1) month, there can be many dates within a short period of time and if the chemistry is there Aaron will not hold back as you have with Jen. At the very least they will develop a friendship and if your fantasy were to become reality she will eventually lose her virginity to Aaron. Know that you’re playing with matches/fire.

As another posted mentioned, at some point Aaron will ask Jen what her boyfriend's name is, and Aaron will get a shock to find out it is you. If I were you, I would talk to Jen and suggest that she give him Aaron another name so that he would not know it was you this way when he talks to you and your friend about the girl that he is now seeing, he will speak much more openly around you. Either way, it will be a tricky situation and anything may happen when Jen learns to feel good about loving you and Aaron at the same time. Hopefully you will be able to handle everything with regard to the emotions without becoming jealous. I know others have mentioned contraception and unplanned pregnancy, this is something to consider just in case, always have a plan for how you will be if it does happen.

As to Jen’s lunch date with Aaron today, hopefully all will go well and they will have good chemistry and decide to have another date. When you speak with Jen following the date, do not push for details, open yourself up and do a lot of listening. Have open conversation, talk about how she feels about this new adventure, this journey. Does she has concerns and or issues with playing our your fantasy, etc.?

There has been a lot of talk about your fantasy, you have said that Jen is a virgin. Are you also a virgin?
 
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Daniel97 said:
Jen is on her date with aaron and I have masturbated multiple times in last last hour thinking about jen on her date with aaron.
since its their first date if you call it a date, nothing will happen yet just thinking about them is too much for me.

I wonder if they have gone in Aaron's car, and how good it might feel to her sitting next to a tall handsome man with a car licence?

I wonder if he might hold her hand, brush her shoulders gently, or open/close the car door for her?

He might sneak a kiss, something he might be good at from having a steady girlfriend for 18 months.

I think conversation will flow easily between them - I can't imagine Jen/Aaron being tongue-tied.

:love::call:
 
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Jen will have often thought of you removing her bra completely one day in the future, and also you getting curious between her thighs, so her mind will be primed if Aaron seeks an opportunity. Just takes a man with seduction skills, and love stories she has read can suddenly become real like turning on a light switch.
 
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Jen came late after date, I tried calling jen at 6 and 8 but she did not pick up and messaged me that they were still on date I was surprised that they were out for so long.

Later i was able to reach her and talked with jen about her date, she was bit reluctant at first but I ensured her that it excite me to hear what happened in their date and I won’t feel jealous. She told me there is nothing to be jealous about as I told her to date aaron. She told me Aaron picked up jen from her room and they went to eat (nothing special just a small restaurant). Jen and aaron talked about many things like hobbies, hometown, friends, relationship etc.

Jen told me aaron ask if she have a bf she replied she doesn’t have a bf, but during the date she stared feeling bad about deceiving him and told him she have a bf but he went to different college and they kind of allow to date others and this was her first date with an guy other than her boyfriend. Aaron ask her if this is her first date then it should be special and they should not waste it by watching movie.

They traveled to few sightseeing places and then went to Mt. Washington to take the view of the city. She told aaron it was beautiful and aaron told her he know even better view but jen told him it was getting cold so they should just enjoy this view and then return. They talked for little bit and suddenly aaron kissed jen she was not expecting a kiss, she was startled and fell down on her ass. Aaron apologized for kiss. They took got in aaron car and returned to city aaron apologised multiple times and jen let him know it was ok and reaching home she told me she gave him a kiss on cheek and aaron asked if they can hang out again and she replied sure.

She asked me if it was ok that sge agreed to see him again, I told her it was totally ok and I was excited about hearing the details from her. She told me aaron is a nice guy and just got over her relationship with his old girlfriend its not good to play with his feelings like this. I told her ok just next time you meet him let him know that your bf want her to date others and sge is not sure if her relationship with aaron will become serious or not and if he still want to date her or not.

Jen thought about it and then agreed it was the best action as it will give aaron atleast some information about how far their relationship can go. I asked her so how far is sge willing to allow aaron. She got angry at me and asked how can I even ask her that question and she won’t take it further than a kiss and bit more. I apologized and asked her if aaron wanted more (definitely a wrong question) and she told me aaron will understand that she is already in relationships with other if he continue to date her he will know the limit of their relationship.

I asked her how does kissing aaron felt like, she was surprised and asked me if I really wanted to know it. I told her I want her to date others guys and then tell all the details to me, I might get jealous but I love her much more than she can possibly think and little jealousy wont do anything and its excite me to know about the details.

She told me after reaching the hill they were leaning on the car and talking to each other when aaron put his hand on her and she did not move his hand as it felt worm and fine. Then she turn to aaron and he was looking at her maybe he took this as a signal and suddenly kissed her. She was so embarrassed by it her face was hot and red throughout the drive back.

Aaron also asked if they can sit together during the classes they shared and she said it was ok. Then she asked me if it was ok I told her it was fine. Then we talked a bit about other things and ourselves then I suddenly remember and told her to not give my name when she tell aaron about her bf. Then we talked some more and went to sleep.

I am unable to sleep and want to masturbate more thinking about her and aaron but today I must have masturbated almost 6 times and my cock is tired and balls are empty so now I am in bed writing this still unable to sleep.

is too much masturbation unhealthy?
 
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Congratulations! It definitely looks as though you've gotten the ball rolling, Daniel. Thanks for sharing the details.

Daniel97 said:
I am unable to sleep and want to masturbate more thinking about her and aaron but today I must have masturbated almost 6 times and my cock is tired and balls are empty so now I am in bed writing this still unable to sleep.

is too much masturbation unhealthy?

Eh, just enjoy yourself while you're still young. I wish I could still do it six times in a row...
 
Daniel - Congratulations on Jen's first date with Aaron. At this point I would not push her, allow nature to take its course and provide encouragement and support without being pushy. Thanks for sharing the details.
 
SquirmingSub said:
you have said that Jen is a virgin. Are you also a virgin?

hi SquirmingSub, i am also a virgin.
 
Daniel,

Thank you for answering the question, hopefully you did not take it as intrusive or offensive. With both of you being on the younger side of many of us that post on the site that have extended experience in this area, I was simply curious as to what your overall goals were.

Looking back at the thread, with the possibility that Jen could lose her virginity to Aaron or another guy at your request, you two will not have that opportunity to lose your virginity to each other respectively. Lets look at this with rose colored glasses, if she were to connect with Aaron in a such a way that he becomes her friend with benefits "lover" while in college and lets assume that she does not tell him that you are the boy friend, assuming that she maintains her relationship with you and assuming that Aaron is open in conversation about his FwB/GF to you and your mutual friend are you going to be able to handle heading about the relationship from Jen and Aaron? Are you going to be able to handle that possibility that even if you two stay together that Jen may not allow you the same privileges of intercourse that Aaron may have exclusivity to during those college years.

Are you ready for your fantasy to become reality?
 
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Daniel97 said:
hi SquirmingSub, i am also a virgin.

It is great that you freely admit you are a virgin without you pretending you are not.

The fact that Jen got red faced and fell over and couldn't "clear her face" during the drive back, means she needs to have privacy to experiment sexually without having to give a morning talk to you in detail when she gets back.

I knew that Aaron would try to kiss her at the first opportunity, and she admitted kissing him when they got back, so that is a great indication they could be good for each other long term. Jen has consented to sitting in class together and having more dates.

Jen and Aaron will paddle their own canoe together from now on - they are on the same page. They like each other.

Jen said Aaron would know what the limits were, kissing and a "bit more". She obviously expects he will want a "bit more" than kissing - and she will give him that chance.

You have to be very careful now that you don't annoy Jen from being too involved in their relationship. If you want Jen to lose her virginity to Aaron, you must give her the space to let the desire to be fucked by him grow in her mind.

It has been you and Jen for so long, and the best you have done is feel her tits without taking off her bra.

Jen/Aaron need to develop their own brand of loving without guidance from anyone else.

When Aaron heard that Jen has another boyfriend, but he is letting her date other men, then he said they should do something special together - and they did.

Jen will already be seeing that Aaron likes her heaps and heaps - and he will take her many places where they can park for hugs and kisses.

Give some thought to acting more like a cuckold, as though Jen/Aaron are already a loving couple who have been dating/fucking for years.

Jen/Aaron need space to "get some weeks" into their relationship, so they reach a point they fall asleep every night thinking about each other.

You have told Jen to forget about you when she is with Aaron, so it is just her/Aaron alone having a good time together, enjoying themselves.

If Jen is wearing any friendship rings or pendants around her neck to indicate you and her are into each other, then you could suggest she take them off for the month's trial, so she does not have to feel guilty dividing her emotions between two men.

You talked Jen into dating Aaron, so you need to step back a bit and give them the special privacy they need if your fantasy of Jen losing her virginity (to someone other than you) is to take place in 2015.

Let Jen/Aaron become addicted to each other (from the passage of time), so they can share their sexual fantasies with each other without telling you.

Read as much as you can on how to be a perfect cuckold, and let Jen push your mind around.

Jen probably won't tell you for a few months after she begins having sex with Aaron - and it is probably best you don't ask her if she has. A true cuckold waits to be told - he doesn't ask.
 
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Sarah - as always you give great advise. Hopefully Daniel will take your pointers to heart. Once he embraces being a true cuckold he will always crave it.