Repaying Debt with Sex

We had to cancel our date at the end of May as she was ill, but have now arranged to go out on June 30th. We mange to meet up once or twice a week to chat and we now kiss properly every time.

Last week she texted me at 3.30 am, although my phone was off and I didn't receive it till nearly 8. She said she couldn't relax and had been reading the cards and notes I have sent her and was writing a few lines in reply and hope it would make me smile. Haven't got her note yet, but I am quietly optimistic that her resistance is crumbling. I hope she is nearly ready to sample my cock.
Peter C

Have had to cancel tonight's date - me this time. It is so annoying that we have one only managed to go out once so far, but unfortunately my wife knows where I am 24/7 which makes it difficult to meet Rebecca. Still texting one another though.
Peter C

Becky's note to me:

"Just a few linesto let you know how much you mean to me. I don't know what I'd do without you. I know I still owe you that money and really want to get my debts and rent arrears clear so I can move to be closer to you. But I don't want you just for money. You are very special to me and I will never forget what you have done for me. Wish I could do more for you, but I'm not into getting heavy. I'm not like that. I feel sorry for the way you are treated by Debbie. You know you will always have me, even though I'm a pain - I'm always here.I think about you all the time. Don't give up. Things can only get better. Loads of love, Becky xx"

What do you think? Am I wasting my time or should I keep trying t get into her knickers?
Peter C

Any update Peter? Sounds like she is not going to let you in her pussy.

It seems amazing that 9 months has now elapsed since I last posted here. I must be more patient than I thought, as I still haven't fucked Rebecca!

We have been out though. We always kiss passionately and I have stroked the top of her breast and groped her ass. I have asked her outright to relax with me and I she is on the verge, but she wants to move first. This could be as soon as next week and her texts imply that she wants to see a lot more of me once she is in her new flat.

I want to see a lot more of her too - naked preferably! Hopefully, she let me take a couple of pics for you guys to see.
Peter C

Thanks for the encouragement Jas. I expect a lot of guys think I'm going too slow and won't get there, but "softly softly, catchy monkey", I am now very confident that I will soon be in Rebecca's pussy. She and my wife have drifted apart and never see one another now, so that is helping me.

Good luck with your pursuit of Emma too!
Peter C

Peter, thanks, good luck and keep us informed on how you get on!

Peter. I've been in a similar situation and although I've not fucked the girl concerned, I have had a LOT of fun with her with plenty more to follow I hope.

It's a few months since your last post, do you have any news to report from the new flat?

Rebecca finally moved to her new flat last week and already seems a lot happier and more relaxed. We have arranged to meet up next Saturday and I wouldn't be at all surprised if I have something to tell you after that.
Peter C

Peter, any news?

Sadly, no. I did take Rebecca out for a meal, but didn't get into her flat as she was decorating it and her mister (who doesn't live with her) was on his way over to stay. Another problem is that her new flat is further away from me than her old place. I have to plan ahead to avoid my wife getting suspicious and restrict our dates to monthly, as I rarely went out before. Our next date coincided with her mister going camping - excellent, I thought - but I cuckolds brownie out again when their was a family row and he didn't go.

That said, we are even closer with texts exchanged daily and when we met the kisses are very long and passionate. My hands get inside her top to stroke her back and belly and she lets me cup her breast. I will get there I'm sure!
Peter C

anything new to report peter?

WELL...
I read this entire thread ,wondering how and/or when it would relate to the theme of this forum. Maybe reverse situation where the man "cucks" the wife?? Ummm...that's just the historical state of affairs and not at all uncommon nor newsworthy (Dog bites man) Or maybe wifey finds out and hubby is made to REALLY pay for his cheeky attempt?
THEN IT DAWNED ON ME....Mate,Rebecca has been cuckolding you this entire time!!!! And, tell me if I'm wrong: but I think somehow you know and get off on it,...heeheehaha
Read some of your other posts,too. Maybe you should transfer the repayment of the debt to your bull mister, tell Rebecca she now owes him...and see what cums about!
Who's Your Bitch.single,cuz not man enuf to attract a woman.
Will meet for sissy sex with yor cuck!!

YES ,HOW DID THIS ALL WORK OUT IN THE END?
SJB

had this thread saved in my favourites. shame it hasn't had a 2009 update but this is the first time i've been on here for months so maybe he will come back.

lol someone e-mail him! lets see what happened!

Well. I can't believe it has been over 5 years since I started this thread and 3 and a half years since I last updated it. I did carry on seeing Rebecca and we did become very close, but I'm sorry to report that I never got to fuck her. I have a lot of photos of her on my phone, dressed and in her underwear, as well as a couple of her topless. She had such a lovely little slim body - small breasts (which I like anyway), though a little saggy and a sexy flat tummy.

I'm not sure if she was very cunning or I was just very stupid, but I ended up giving her money every week, paid her phone contract and bought her clothes and jewellery, in the hope that I would bed her. Things did move along a bit. I saw and held her little breasts a few times, fondled her bare, tight little arse and even managed to brush my hands across her pubic hair once when she had pyjamas on and no underwear.

I remember meeting her one day when I had deliberately adjusted my underpants and when we cuddling, I unzipped my flies. I guided her hand into my trousers for her to touch my penis for the first time. She seemed to like holding my cock - said she was "buzzing" - and stroked and rubbed it up and down for awhile. This became a regular thing with her even instructing me once to meet her with no pants on so she could get hold of my cock easier.

Sadly, real life kept getting in the way. Her teenage mister - unfortunately so much like his "psycho" man - moved back home with Rebecca, which made it much more difficult for me to visit, plus one of my flowers got suspicious after borrowing my phone one day. However, the crunch came when I did my back in at the end of November last year and I had to text Bex to let her know that not only was I off work, but I was house-bound too. Coupled to that, my wife decided to check my phone one night whilst I was arelax and discovered my relationship with Rebecca.

My wife didn't go as mad as I thought she would, probably because she'd spent much of September and October with a toy-boy lover herself. She made me delete Rebecca's number though, but must have also texted her pretending to be me ending the relationship and slagging her off. She did a very convincing job, as I received a number of nasty, vindictive texts and messages from a very angry and bitter Rebecca.

I have not heard from her since December, but I would still like to see her again, if only to put the record straight. I'd like to think our relationship helped her, made her more confident after previously being with men her own age who treated her badly. I do miss her, but to be honest, financially she was reding me dry. But then you know what they say : "there's no fool like an old fool."
Peter C

Sorry to hear that mate. To be honest when I read this the whole "paying off her debt" thing set off a big red flag, but then as I read through the rest of the topic I thought maybe it was working since you hadn't mentioned giving her any more money or anything (except for taking her out).

But if you spent ages giving her gifts and money and stuff regularly then it is much more likely that she was taking advantage of you (especially since some of the excuses she gave for not relaxing with you were a bit dodgy).

Having said that - if she spent all that time with you - even if you were giving her gifts etc - she probably did enjoy it and benefit from it. Plus because your wife broke things off it's actually impossible for you to tell what she thinks.

And finally - you had a lot of enjoyment from Rebecca over the years - perhaps that was worth the money you spent?

Culum Struan

Thanks for your thoughts. I'm sure Rebecca did enjoy my interest in her and my company. Although there was always that thought at the back of my mind that she was just stringing me along for the money, a kind of "sugar daddy" figure, there were often times when she say something unexpectedly to make me think we definitely had "something". Such as her comment one day that she now appreciated "the older man" and could never go back to a guy her own age.

I'm still convinced that I chanced upon an inexperienced woman who had been mistreated by at least one guy (her mister's man) and despite this giving her a mistrust in men, she slowly but surely let her guard down and let me into her heart. In that respect at least, I'm flattered and proud that I've been out with her. At first, she would blush when I complimented her, such was her lack of self-esteem - she just wasn't used to being with a "nice guy". Gradually, she grew to enjoy it and eventually I think I convinced her that she is a pretty girl and that she really does have a lovely, slim, fit body.

The fact that she posed for photos in her underwear for me - she'd never done that before for a guy - supports that and she even found enough confidence, thanks to me, to buy 2 low-cut tops with built-in cups that meant she could go without a bra. The black one was ok, but the white one seemed much more revealing and I loved seeing her in it. She knew that and wore it quite often for me. It showed off her small breasts a treat and from the side you could see not only the slightly tanned top part, but a paler bit, not usually exposed. I loved the thought that other men would be admiring this view and told her so. She confessed that she had noticed one or two guys looking at her boobs, which I liked, and told her to take it as a compliment. Rebecca wasn't one for showing too much in public though and after one guy stared at her exposed cleavage on the bus, she went straight home and changed in something less revealing!

She was also aware of my love of white clothing and her flat belly. Rebecca knew my wife now has an unsightly flabby tummy, so was happy to show me her bare midriff in a nice white crop-top. I tried to talk her into having her belly button pierced, but never quite persuaded her. Nor could I get to wear a short skirt without leggings.

My confession to her that I was turned on knowing that other men would be admiring her tits in that low-cut top was as far as I ever came to telling her of my submissive, cuckold tendencies. I definitely would not have wanted Rebecca to relax with other guys, nor my first wife for that matter. Yet with my current wife, nothing excites me more than the prospect of her having sex with another man - very strange.

I know this Repaying Debt With Sex thread did not really fit in to the normal criteria for this site, but thank you all for reading and commenting on my posts, which have at least given me an opportunity to re-look at the situation and get things off my chest.
Peter C

Hi Peter,

Interesting story! I can't quite figure out if you're the "real" man, or the cuckold (albeit in an odd manner). Perhaps it shouldn't be said, but I would say that you should just push to get inside her pussy. A lot of women fantasize about being taken by an older men - I can tell you that my girlfriend fantasized about being a "green leaf" for a landlord whom we couldn't afford to pay back!

Maybe I was too submissive to push Rebecca further. Perhaps I was too much of a gentleman to demand she got on her back for me. If she wanted more money that much, there's a chance that she would have opened her legs, but I didn't want it to be like that.

I'm pretty sure Rebecca did not cuckold me, whereas my wife does. There are some that would say I'm not much of a man, so maybe the wimp in me cost me the girl.
Peter C

A picture sent to me by Rebecca from her phone.
Peter C

Another picture of Rebecca's breasts she sent me.
Peter C

Rebecca's breasts look good in this pic. A nice white bra with her bending forward. Made her tits look bigger than they actually are.
Peter C

A pretty bra and Rebecca's lovely flat belly.
Peter C

Try that again!
Peter C

A sly shot I took showing how much breast that white top tended to show.
Peter C

And I know a lot of you want to see her face, so...
Peter C

She's nice. Lovely tits. Shame you never got to fuck her!

Peter

Sorry to hear it ended like that. Like most of real life, there are not many happy endings. As for "no fool like an old fool" I think the age is irrelevant when it comes to sexy women. Maybe it should be "no fool like a horny fool" and then you will be in very good company! Probably most of the men on this site!

Isn't it funny how our wives aren't keen on us getting a little extra despite all the extra they get.

syncro