Promising chastity to my ex.

So I have known this woman for 3 years, co-worker manager of mine. We went out for a month, (best sex I ever had) we were a couple. Well 2 months later she was in another relationship which lasted 3 months. She commiserated with me her frustrations and problems both in and out of the sack.

At this point I realized I was in love with her. I know the guy could last and do her whether she wanted to or not. She believes she should please her man to keep him interested. I was lacking in the take charge part. Well she broke up with him, much too every one happiness.

Well she joined a dating site, I saw her matches and almost all would be a Bull. Me, I am cuck materiel, that's why I am here. I let her know that I haven't been laid since our break up in May, that I was really frustrated. that I have a hook-up if I want. She dis-approved, she wont judge but she doesn't like the idea of me relaxing with a one nighter.

I told her, her opinion of me matters to me and that I will skip this hook up for now. I am thinking of messaging her back and saying I promise to her no more sex till I am in a relationship. I will also admit to now feeling like her girlfriend. All while knowing her new love interest is coming to town this weekend. She is over the moon for him and she hops in the sack very fast. I on the other hand could be single till I am dead.

She said he is the most amazing guy she has ever seen, no comparimister. I was hurt, jealous, turned on and shaking all at the same time.

Can you say I enjoy humiliating myself.

You might as well come out to her and tell her your fantasies. Do you think she could handle it? When it comes down to it...do you think you could handle it?

Well when we were on our vacation in Cali over the summer; after we broke up, I almost came out and told her my fantasy of seeing my girlfriend/wife as the cream in the oreo cookie. I would sit and watch as two hung black guys serviced her bareback all three holes. One a young guy and the other old and fat. I told one female friend, I can handle it but I don't think she could. I did let onto her that I didn't think I could be man enough for a woman and could handle another guy servicing her. Her response "get therapy!"

At some point if you will have to tell her something. If you don't, she might not know what you really want and may move on. It might be one of those...you snooze you lose. Find a subtle way of getting the info to her by talking to her. Have her over and watch a movie with wife cheating in it..."If you were my wife, I would let you..."

Well here's an update.
I messaged her the other evening.

me. So I been thinking.
Her. Yes. What have you been thinking.
me. As much as it frustrates me, I will stay frustrated rather than have any more one nighters. I will wait till I am in a relationship.This may mean I will be celibate till I die but I promise you no more relaxing around. This just means I will have to live vicariously through you and...
Her. You are a love. Know that.
Me. Thank you

So I do know she cheated on her boy friend of 5 years with a coworker. Who wound up treating her like Shit!:mad: I hate that guy. She has three different guys shes seeing in the next two weeks as well and some guy did a booty call on her.

This is a chance for you to have some fun as well. You should ask her to put you in a chastity device. This sounds like she an opportunity to start a great cuckold relationship with her. Tell her you can provide the stable regular household, be her loving, supporting husband...and cuckold. You can provide everything she needs except the great sex...that is for her lovers.

This is very erotic... Keep us posted on what is going on.

I agree; very erotic. But don't make the mistake of assuming she will be into getting this more kinky just because of what has happened so far. He disapproval of one-night stands, her commitment to "pleasing her man," and her "get therapy" response to your comment about the idea of cuckolding could all add-up to a traditional mind-set about sex and relationships that will never be interested in cuckolding, erotic offense, or a chastity slave on the side.

If you think about it, she was approving of your pledge not to have sex until you are in a relationship. Opposition to promiscuity is not kinky. (If she had approved of the idea of you not having sex until she was in a relationship with another man - or married to one - that would be kinky.)

It seems to me that you have a very straightforward choice here: Either you make a kinky proposal and see if she goes for it - risking that it goes badly OR you just enjoy the vicariousness you already have.

If you do the first, I think the idea suggested by Allen is good. Tell her you are thinking of getting a chastity to help control yourself until you are in a relationship but you need someone to help you by holding the key. If she agrees to hold the key, you can maybe engage her in a conversation about how often she thinks it might be appropriate for a single, celibate man to masturbate, since she'll need to help you stick to the scarbonsmudgedule by only handing over the key at that interval. Who knows where it can go from that. (For instance, as you go forward, might she not need to verify that you have re-locked? Eventually you might combine the vicariousness of her story-telling with your release - she might believe that telling you about her and her man as jerk-off material is an outlet to prevent you from living out the cuck fantasies she knows you have. Etc.)

If you do the second, my advice is not to try to meet people or get into a relationship for a while. If her relationship goes well (letting you enjoy all kinds of vicarious action) she will eventually turn her mind to matchmaking for you. As you slowly share you fantasies and submissive side with her further, she'll add it up and try to find the right woman. Also, never underestimate the *** jealousy an ex like her may feel and the interesting way it might shape her set-ups for you. Think of the thrill of dating a woman you aren't into because your ex wants it - especially when you have to share all the explicit details with her!

Good luck.
Pantalone, Wittol, oblate, abnegator, fellator, pathic, irrumatiophile,fop, epicene, cotquean, skivvy, thrall, and pilgarlic.

So here's an update. Last week she went shopping for her first meet with a guy she met on the internet. Well she sent me pics of the two sets of bra and thongs sets that she bought. One black that I recommended she wear and red. Her other guy friend recommended black as well. She got some nice boots to go with it.

She was all over the map this week is he coming or not. with her other guy friend what condoms to buy. She always left that for the man as his responsibility. So I was all super eager about this and asking questions. Well the next day she let me know she is a lady and expects better. She isn't, that's why I love her.

Well yesterday he arrived. they did the usual meet and greet, talked and walked. dinner listened to jazz. Had some takes. Here is the rest in her words as we bbm'd

Her. We were tired & planning to hang today so we left & kissed before we got in the elevator. I was praying no one would join us and we awere alone. And it was electric. And he asked if i wanted to come up to his room for a little while. And it was incredible..three times in a row. And then I cabbed home.

Me Awesome, he unwrapped his present? Did you go with red or black?

Her. I followed directions from you & **** & wore Black. Not that it mattered. he did notice after the fact. I admitted I bought them for him.

Me.Yes!! and you were happy with his package?

Her. I was happy with everything. It was extremely passionate, intimate , intense and fulfilling.

Me. That's so awesome I am so happy for you. And 3x. What a star. Did you use your condoms? So I take he passed the oral then?

her. No oral. And yes we used condoms. A lady doesn't kiss and tell. Not **** remember.

Me. I know ... just...

Her. I am preparing my self to go to the hotel & him be gone.

then other stuff from there, when I referred to her as a present at first I thought she was pissed, well she was flattered.

This is getting good. Do you think offering to buy condoms for her, or finding other ways to assist her would be a good move?
tony

So she went there and they hung out for the afternoon before he had to go home. When they ran out of things to do they went back to her place and watched football. Well one thing led to another and all she wanted was to be kissed and make out. Well they had sex and he tried to ship the condom but she wouldn't have it. So on it went and he shot in 2 min.

She wasn't happy, she said it was great but 2 min, anyway she was left feeling empty. I asked empty as well as used? Yes, well he barely kissed her good bye. He used her for sex. Well that was Sunday and tonight she is on another date with a new guy from the same website. She was messaging him last week.

Has there been anymore mention about you staying frustrated?

Well over the Christmas Holidays the guy contacted her said "Hope Your well and have a Merry Christmas, Kisses." Well, me and all her friends told her to tell him to F' off! She responded by asking "Is this a joke?" His response was along the lines of I thought you just wanted to be friends, and I have been super bus that's why I never got back to you. She is done with him

Well the guy she went on a date with from the same website, well she showed up late after a nightmare day at the office got her make up done by a gay guy at the have store across the street and wound up having an amazing time with him.

We met up over the holidays and tells me this she is trying to see if she can see him before he leaves for a week. Some how the condoms came up in conversation and I offered her my supply. She didn't respond. I let things be.

Well she took the ferry home and turns out he met her and well she was happy they got cozy and eventually wound up in her car making out. Very cumbersome as its a hatchback and she is small and he is 6'2. She is over the moon. She tells me how she has a date with another guy for last night Wednesday and thinks she should cancel. I heartily agree.

Anyway he contacts her and she lets him know her evening is free. I tell her he is totally interested turns out they will watch the game at her place. I know this to mean he will be boning her, she is a **** after all no matter how much she protests. I get a message at 10.30, off to bed what a great night.

This morning she spills all the details, how attentive he is etc. He wasn't prepared, she had her arsenal of condoms though. I offered mine as they were just sitting there. She messaged him and let him know what an awesome time she had and happy Birthday etc. She also admitted to being worried if she would hear from him. Well its, and still no word. I talked to her and we both agreed she needs to (her words) "Keep her pants on".

I am going to drop hints about being frustrated over the next few days and see her reaction. I did say to her once about how I am sure not many guys promise her celibacy, she was uh no, your the first.

Any updates???

Well she is still in contact with the last guy and she mentioned he wasn't that good in bed but if she needed her itch scratched she might hook up with him again. :mad: He treats her like crap and isn't that good in bed either yet she may relax with him again. I said no, there are other candidates, as in hint hint, nudge wink...

I have mentioned my 8 months of no sex several times not to much avail.

So this weekend I went and visited her. My agenda after losing alot of weight was to by some new clothes. While we were looking for clothes we passed the lengerie section. I helped pick out two sets of bra and panties for her. I wouldn't let her pay for them either. Told her that was her commision.

Nice, always look forward to your updates.. Do you have any pics of her?

Although we chat every day there is nothing new to report. same old same old.

So the weekend I was over there I took her out to a fabulous Italian restaurant, wined and dined her. The entire time we were together her cell was going off with messages from a guy she had played scrabble with only a few days before. Well we got takes, and I told her I loved her, would move for her and quit my job for etc. I paid the $250 bill. All I got was a kiss on the lips.

I knew the guy wanted into her pants with the messaging all night, as she kept telling me. Well today she admitted that two days before we together, they had knocked boots and it was good. So the entire time we were together that night I was a chump. I had not the slightest chance.

This is our conversation today via messaging.

Her. D is coming over this afternoon. He wants sex. I am considering using him and kicking him out. He is a great looking guy why can't he find some one else?

Me. Well its your call. if you want your itch scratched with a hottie go for it. just remember,once he's had what he wants he Will be gone. And if you want to use I say go for it. Just be safe and have fun. Is this what you want?

Her. It will be spiteful isn't that bad? i am already planning how and when I will kick him out.

me. Yeah, be safe and have fun. I bet he will try for a fwb relationship.

Her. We'll see. that's all I could see him as anyway. I know you'll be furious but I just wish ** would text/call (this is the dude who used her over christmas and never called, for over a week, messed her up, see above.)

Me. Not furious, not at all.

Her. I would rather have 50 coffee/take dates dates with ** than have sex w D. And sex with D is good. Sorry tmi.

Me. No its not tmi. When did you two seal the deal? If I may ask. That actually changes things then.(light goes on for me)

Her. I have seen him twice figure it out.

Me Ah, scrabble night. (footnote, this night she was hoping they would kiss and hold hands. )
Hope your not pissed at me. but I now understand where he's coming from and all that.

her. No I'm not pissed. I didn't say anything because I thought you would judge me.

Me. I am not judging you, I understand his behavior now is all. Who am I to judge one of my best friends. Beside you have run circles around me. If anything you should be judging me for my failure to get even a second date.

Her. I would never judge. I am neither here nor there w D. And dont feel like spending that much time with this guy.

Her (4 hours later.) Not even 2 min. No lie.

me omg seriously? No call backs for sure. And what are you thinking?

Her. What a loser. We laid in bed and talked for 45 min. He wanted to stay but seriously?

I keep checking for updates on this every day... Blocker.. would she ever limit the amount that you are allowed to play with yourself?

Well I admitted to her that we were effectively girlfriends, short of braiding each others hair. She was amused and totally agreed with me. We talk about everything.

So last week she was out here for her birthday and was going to meet a guy in the U.S. before she wised up. So for her birthday she spent the night at my place where we wined and dined and the next morning I gave her an expensive birthday present. Well she went home to her family that night and went out with a young hood friend to the bar.

So her friend and her are takes, and in walks this cute guy and her friend is digging him. So my girl tries to get him over and play pool with them. Well one thing leads to another and they wind up talking all night leaving together to his place and making out all night and talking. They met a couple times more and she was really digging this guy till he came clean and admitted he had a girlfriend. She was pissed. As she is telling me this over the phone I am wanking.

She has two dates today so here is hoping. I will message her in a few days and say I found a girl on craigs list who is interested in sex only and I need an executive decision from her. But I don't want to break my promise to her, that I aint had sex since may. If she says yes I will say, your supposed to say no, this is my self destructive behavior. If she says no, then thank you, thats just what I wanted to hear.

Thanks for the update. Good strategy on the Craig's List thing. Just make sure you don't do anything and she knows you don't.
Pantalone, Wittol, oblate, abnegator, fellator, pathic, irrumatiophile,fop, epicene, cotquean, skivvy, thrall, and pilgarlic.

Blocker, Just wanted to check and see how things are going? Have you talked with her about the Craigslist girl yet??

So turns out she had two dates Last Sunday. On at a bar to watch a hockey game then one at her place to watch the oscars. Well she made out with the guy at her place, though neither was interested in sex. She told him about the guy a 1000 Km away. He said pursue and if he is the better guy be gentle when she breaks it to him. She thought that was adorable.

Blocker..... how are things going??

So I just got off the phone with her had a 38 min conversation. Well she had the guy over again and they hung out. Code for sex, well he did a good job enough to spend the night. They talked about how she is going to visit this guy over a 1000km away at the end of the month and see how things work out with him. He wants her to explore and see what happens and if it works be nice when she ends it with him. This makes five guys she has been with since me. Only because I am still not with her.

We talked about affairs and how I would be okay with a physical affair (well duhh that's why I am here.) She wouldn't stand for either and yet she has cheated in the past and slept with this guy and made out with another while being invested in a guy over 1000Kms away.

I told her about me trolling craigs list. How its been since May since I last got laid. I told her about regressing into bad behavior and breaking my promise to her and myself. She said I need to live in the now and go and explore and how different it is for guys, how we need sex. She said lets talk tomorrow and hopefully post orgasm.

I also told her that I felt left behind as she has had 5 guys since me and I aint even kissed a girl. What a loser.

Any how. Thats it for now.

Blocker.... Is she saying here that you should be going out and finding sex?

Whats the latest, Blocker?

Did we loose blocker????

This is after a conversation where i told her she was the best I ever had in bed. All text.

Me. last night when we were talking I told you that you were the best. You were< but you didn't say anything about me. I know I excelled in some areas. But just be honest, how was I? And no need to sugar coat.

her, You were great. I didn't say anything because you are my friend. That part of my life is done. I am not comfortable talking about it because I don't want to encourage any ideas that maybe there could be something in the future. I don't categorize best or worst. I just don't operate that way. i told you we shared a good connection I don't know what else you need me to say. I have told you that you are large and have a nice cock.

Me. okay fair enough. I respect that.

Her. I am so frustrated right now. Even if I told you I think you were the best lover in the world you would neve allow yourself to agree, that I can't do anything about.

Me. I appreciate that. Erm sorry for frustrating you. And your right. Sorry for being a bit of a douche.

Her Douchiness over looked.