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Honesty is the best policy when meeting a new girl

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torontoboy

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#1
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I met a new girl off an online permisterals ad the other day. I still can't believe how fast it's all happening, or how I somehow piqued her interest because I would definitely classify this woman as way out of my league; confident, smart, extremely hot (Oh gawd, what an hourglass curve...), and sexually experienced. What makes this even more surprising is that she clearly stated that "size does matter" and that she is searching for a well endowed man with a fit body.

Although I might have intrigued her with my words initially, and then my voice on the phone, I thought I should be upfront and honest and disclose that I'm not quite the man she listed that she wanted to meet -- I may be healthy, but I have skinny arms and certainly no six-pack abs -- but more importantly I only have an average sized penis; and actually from what I've found out recently I'm probably on the low end of average at 5.75" (although I didn't mention that specific detail). Suffice to say, I was open that she would probably have been with larger guys, but although she was a little worried (there was a lot of discussion around how "small" is average anyway) especially since she remembers being with one guy who she described as "not feeling anything with" during sex, it seemed that the fact that I was being open about my penis (and not hung up or ashamed about it) was raising her interest in me. In fact it spurred her to be more open with me, and then we had a long chat about our sexual histories (she is way more experienced than me, although she is only 2 years older than me; she's no bed hopper or slut in the typical definition, but certainly a bit of a "bad" girl!). Then, to top it all, she surprised me by suggesting we meet that evening for a casual dinner out.

Meeting her and dinner was fun... we clicked and had lots of great conversation (non-sexual for the most part, although somehow it came up that I had a foot fetish and she thought she should shoe me her feet to get my opinion... aside: her feet were to die for!! -- although i tried to act nonchalant and comment how how perfectly proportioned they were and what nice nail polish she had on), but she openly made some jokes every now and again alluding to how I probably had a small penis (e.g. commenting that my feet were small for a man, or at one point I mentioned that something was a "tight fit" in a certain context then she twisted it back slyly by saying "i bet you've never heard a girl tell you that" -- ouch!). But it was all done in a playful non-mean way.

I genuinely feel that she is interested in me. She's texted me and called me 2 days in a row -- in fact she wants to meet me again in a couple days. I know I'm digging her for sure... I just keep thinking what lottery did I win here... there's no way I would have been able to approach a woman like that, let alone get her attention if I had met her in normal social situation.

Anyway, I have to admit that I'm a little nervous about how the first time will go... as I strong feeling it's going that way very soon... but it's the type of nervousness that turns me on! What if she does truly find me small, all joking aside. To me, it will be a challenge and will spur me on to try harder, try other things (oral, toys, hands, etc.) to get her off. It also turns me on to know that she's been with bigger guys...

She mentioned once during our initial conversation where we exchanged sexual fantasies that she's never tried a MFM threesome. Perhaps that's something I could suggest one day soon if she becomes my gf and if she finds me small... I'm sure she will not hesitate to try it, she's very open-minded (and it's her fantasy after all)... and who knows, I may just end up a cuckold...

All this because I was honest...
Allen

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Posts: 3098
#2
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good luck and keep us updated. thanks.
torontoboy

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Posts: 20
#3
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Thanks for the feedback Allen. I'll definitely update this thread and let you know how things develop.

We had another long telephone conversation last night; one that was only meant as a few minute chat about when to meet again turned into hours. She even remarked how she can't believe how comfortable she is talking to me. She's a really smart girl, yet somehow our discussions tend to end up turning to sexual topics; not quite dirty talk (although it gets me horny with the visuals), but more academic I would say. For instance, the topic of Kegel exercises came up (apparently she's never tried them).

I found out that she's primarily dated and been in relationships with black guys. She's half-black herself; actually I really don't like these colour references since I hardly consider myself "white" (it's more about the cultural/ethnic heritage to me, in my case mediteranean). I don't particularly have the fetish some people have about interractial relationships, but it is still a bit of a turn on to be "an exception" to her pattern...
torontoboy

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Posts: 20
#4 · Edited by: torontoboy
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Holy moly... I can't believe how hot this girl is. Nor how fast things are happening! We had sex yesterday -- yes, already. I've never gone to bed with a girl so fast (I just met her 7 days ago!), let alone with a girl who is so hot, out of my league really.

I went over to her place without any expectations, it was supposed to be just a chilled out evening watching a movie, eating take-out, taking refuge from the rain outside. We ended up talking up a storm, mostly about our past, our plans for the future, travel, work, random things really... It was so late and she was so exhausted from her crazy day at work (and a bad night's relax the day before) that we just decided to try to get to bed and relax. Every now and again one of us would toss and turn and we ended up in various close positions (me spooning her, her laying her head on my chest, her legs on mine, etc.)

But it's only by morning that things took a real sexual turn. I initiated a kiss which turned into some serious making out and dry humping (I had kept my clothes on all night, jeans and all). I took the lead and was the one teasing her. She was like a dog in heat and clearly getting very turned on! I think it's partly that it's been so long that she'd last had sex (longer than me even!)... Well, after a break for breakfast, and back in the bedroom to relax a bit, she came on top of me and, after plunging her tongue down my mouth, asked if I wanted to fuck her -- all the while putting her hands down my pants... To which I moaned "hell yeah!"

And that's when her sweet permistera changed... she ran to get a condom in another room (I told you, I didn't expect anything to happen when I came the night before; I hadn't brought any with me) and when she came back she was another permister. She took charge... telling me that if she let's me fuck her that I better not cum right away, asking if I will make her cum, and telling her that I better do a good job... I don't know if she is really that dominant or if she was playing up for me and remembered a previous conversation we had in which I had mentioned that I had never been truly submissive in bed and that I was always curious and turned on about the idea. In any case, I was drowning in lust at that point.

Although partly due to the fact that it wasn't a "thin" condom variety, I really didn't feel much after entering her. But I was getting off on her reactions. She rode me on top with much gusto for a while -- and although I slipped out on two occasions -- she was really getting off. Then things changed... She really took it up a notch. She said "I want you to fuck me from behind", and presented me with the most amazing, rounded firm behind I've ever seen. I then started to go at it and very quickly she started barking at me "harder", "I want it harder". I tried to go harder, but she was not having any of it and said "Is that what you call hard? You better hit me harder!". I was honestly going as hard as I could. Her tone of voice scared me a bit in fact; I was turned on, of course, by her dominant/selfish streak, but was feeling inadequate at not being able to go harder. I scramred to vary my position, my angle... Finally in the end she said "That's a bit more like it". Little did she know I was exerting 110% effort just to achieve this barely adequate level of fucking for a minute or so, trying my best to please her.

I soon tired. She rolled over, inviting me to get on top this time. Unfortunately all that effort started to take it's toll (and probably the fact that I haven't done much aeorobic activity since before winter didn't help) as I started to lose my erection as I re-entered her, now in a missionary-like position. Boy did she let me have it then! "You better get it hard for me", "Come on, I'm waiting!", "Stop holding out on me!", "You better get hard now or there will be hell to pay!"... All the while I'm telling her in a whimpering voice that I'm trying, that I want to please her... For a little while there was a huge disconnect from how mentallying turned on I was (I have never been so mentally fucked and dominated before during sex!) and my penis' pathetic reaction. Eventually I got hard and was recompensed with more of the same demands as earlier "Harder!", etc.

And then she pushed me to the side, in a contorted almost side-by-side position. I stopped to take a breath, but kept my now semi-erect penis barely inside of her. She started to rub her clitoris and masturbate right there in front of me (No girl had ever been open enough to do that with me!). Of course this was no show, this was a punishment "See what I have to resort to, you can't make me cum so I have to touch myself. I'm not even close, this is going to take a long time." She had me watch her while keeping my penis inside of her. "You better not let it slip out, I want you to feel me come." Eventually she orgasmed and I felt a few contractions on the tip of my now softening penis.

We chatted about the experience afterwards and, to be honest, I didn't feel embarassed at all, e.g. about the times losing my erection. She asked in a concerned tone if I felt anything (I assumed that she didn't feel much -- otherwise there wouldn't be any need for that question!), to which I reassured her a bit that yes a bit, but in keeping with my philosophy of honesty with her I told her it was mainly when we first started and she was on top. I never figured out if she was role playing or just truly that demanding during sex; it was just left at me stating how amazed and turned on at how she's a "demanding bitch" during sex; she just smiled mischievously.

I already had inklings that this blossoming relationship is heading in the cuckold direction from the start (see my previous posts), but this got further solidified by our post sex discussion. We exchanged some more sexual fantasies... I was floored when she brought up how she had come across those "please have sex with my wife" type of porn videos/websites and been turned on by the idea. I quickly said that I thought that was very hot, and reassured her that it wasn't weird. She said that she liked the idea of it being "all about her", that she could be completely sexually selfish, yet still have the safety of having her partner there with her. I told her that I had thought about those scenarios too, but for me the turn on would be watching my partner get off, and it being a bit of a submissive mind fuck at just being powerd to sit there passively.

If the growing cuckold undercurrent in our sex and fantasies wasn't enough, as I was about to leave and we were kissing and fondling our goodbyes, she reminded me to get her new batteries for her vibrator (which she'd shown me) so that we could use it the next time we have sex... Then she brought up something from our first conversation (this girl has a great memory!) and said how she is so curious to try things with me "including that cock sleave you said you have" (which I had mentioned buying but never having had the chance to try with my ex before she left me). I had an instant hard on.... If this was not a clear message, I don't know what is.

Of course, when I got home, I proceeded to jack off (as I never did cum during our sexual romp). For the past day I can't stop getting hard as I reminisce of what happened, and wonder about the future with her.

I've never been with a girl like her before. I feel reall lucky I met her! I think she's the ideal paradox that every man fantasizes about -- the good girl (she's a serious, smart professional; she says how she wants to cook me a gourmet meal the next time I come over, she was even a bit worried that I might not be interested in her after we had sex), yet she's a total slut when it comes to sex (she's probably had 30 times as much sex in her life compared to me, she seems to enjoy taking control in bed, and she has very naughty fantasies that have the potential to completely put me in a cuckold role). No wonder my thoughts are filled with her...
torontoboy

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Posts: 20
#5 · Edited by: torontoboy
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Had sex again with her today! She came to my place under the guise of "meeting for a quick coffee", but it was just sex on her mind... It didn't go down like last time, though, more of a "normal" session. Some oral sex to start and then she stopped me telling me she wanted me in her. She somewhat seemed to enjoy my cock (especially when she was on top grinding on me), although she didn't actually orgasm. Neither did I actually -- in fact, I only really felt good stimulation when she was on top at a particular angle. It was quite a close feeling when we cuddled afterwards. I think this could be the start of a really long relationship. It's nice to know that we can have more normal sex too... Though I certainly wish I could make her cum!
Danj

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#6
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Awesome...keep us posted!
torontoboy

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Posts: 20
#7 · Edited by: torontoboy
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This girl is insatiable and very sexual... Well, at least from my very limited experience with women in the past. She invited me to dinner yesterday (she cooked for me, how sweet!) and then we ended up talking for an hour... Out of the blue she just goes: "I know it's been a long day, and I don't know if you have any energy, but I don't care, I want you to have sex with me." Of course, I'm not one to refuse! I have no idea how long we went at it, but I know it was more than an hour for sure. It started off quite normally, almost lovingly, and then it got more vigorous. She really went at it on top of me for a very long time. When it was my turn to "take the reigns", so to speak, I was already getting tired (hey, when I'm underneath, I'm not completely passive, I work at it too! haha) and for a quick moment started to lose my erection. At this point she floored me... Like I said, I was honest from the start, but we never discussed cuckolding explicitly, other than the mention of those web sites (that I mentioned in a previous post), but she started telling me that I might have to be educated in how to fuck her properly. She started talking dirty about how she would open her legs to another guy and let him fuck her from behind, and that she would make me watch as she came hard on his cock. All I could do was groan "no, I can do better, I promise" and get instantly hard again. She seemed pleased with herself when I started fucking her harder again with a magical second wind of energy. At the very least, she now knew the embarassing truth... This really turned me on somehow.

It wasn't until today when we talked and for a moment the discussion got to sex that I commented how I was surprised at her s*******s at dirty talk. She then made it very clear that it wasn't just fictional dirty talk, that she was saying that stuff because she was truly fantasizing about it!!! I can't believe it... I get hard every few minutes now just thinking about this.

I obviously don't think we should rush into anything... I just barely met her after all. Yet it's all developing so fast (both sexual, and emotionally). Maybe we just both feel some sort of unexplainable connection knowing that we've hit on someone on a similar wavelength for the first time in our lives. All I know is that all the signs are positive. I trust her already, and she trusts me. It feels right. She is making time for me and ditching other guys who are pursuing her, and when I'm with her she now is starting to fee like "my girl".
torontoboy

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Posts: 20
#8 · Edited by: torontoboy
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Someone sent me a private message asking if I had fingered her to try to rub her G-spot and attempt to give her an orgasm that way. The answer is no, not yet. Just haven't gotten around to it! But I will try next time!

Not sure why you didn't post on here directly though. If you have any questions, don't be shy, just post it here openly.

Actually I'd be interested to hear people's thoughts about how this is developing. Has anyone been in a similar situation -- where things are developing so fast? This is all so new to me...
jamesriske

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Posts: 1095
#9 · Edited by: jamesriske
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It will be over just as quickly as it began unless you change.

Although she appears to have a high interest level in you for the time being, you are making all the classic mistakes that men make.

When she loses interest and avoids you to the point where she's powerd to dump you, take a few lesmisters from this guy:

doclove.com


,

Flame me now but in a couple months, you'll search for my post and look up the link I just posted and thank me for it a year from now when you finally understand women and how to build a proper relationship.

If you don't have the knee jerk reaction to ignore and flame me, then I suggest that you stop ALL communication with her until you go to his site and read eveyrthing you can about him and order his book.

But I doubt you'll do that. You'll just continue to be a Mr. Nice Guy and whimpus Americanus guy that she will be bored with in a couple months or so.
torontoboy

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Posts: 20
#10
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Hi James: I'm not sure why you'd think I'd flame you. I'm happy you took the time to read my story and pass on your advice. I'm fairly open minded and will take a look at the web site in that spirit. I am indeed worried she might get bored of me, that's why I said last time that I don't want to rush into anything, either in the normal relationship sense, or in the kinky/cuckold/experimentation sense.
torontoboy

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Posts: 20
#11
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I didn't get much feedback after my first post, so I won't bother you with the gory details this time. But I know some of you are reading, so for completeness I wanted to update you on what's been going on.

Unlike what James was afraid of, this does not look like the kind of girl who will easily get bored of me. Quite the contrary, in a weird sort of way, I think I can see a real future with this girl. I know, I know, it's very early days, but also we started up with a completely upside down way of getting to know each other. We started with all the taboo topics, all our flaws, and had lots of sex... and I mean lots (probably more than some newlyweds!) And all along, we have been realising that we are shockingly compatible in other ways; our views, values, interests, etc.

I know I started out posting this thread with the intention of promoting the idea of being honest about one's fantasies right from the start, but I'm starting to believe that, at least partly, I'm just extremely fortunate. I mean, unlike other men on this site who have had to suggest cuckolding to their partner, even "work on it" for years sometimes, or the others who were vulgarly introduced to it by power by their partner (e.g. cheating on them), I have found an open, kinky, and honest woman who happens to share the exact same fantasy as me, who is courageous and confident to talk about it with me, almost to the point of being academic (even though it's all fantasy), but also role play with me about it during sex -- in preparation for the inevitable when this fantasy will become a reality.

I honestly still can't believe my luck. I know I've said it before, but I must have won the lottery with her (perhaps it makes up for all the unfortunate interactions I've had with women in my past!). I didn't even have to bring up the topic, she somewhat brought it up, starting with her MFM fantasy and the mention of certain types of porn. This made it "OK" and non-threatening for me to bring up how I had similar fantasies, and that my fantasies took on a more femdom twist. My girl (yes, I can say that with certainty now), is a cuck's dream... she even knew what a cuckold was before I could even bring it up!

Please excuse me as I go masturbate thanking my lucky stars at having found my cuckold goddess after all these years. Thanks for reading.
for_fun_and_games

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Posts: 97
#12
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You are definitely in a very exciting time. I never really hid my cuck tendencies from my wife when we started dating. I was actually getting a lot of pussy at the time and was just figuring out the whole cuck thing myself. So I never really thought about filtering it. When we started seeing each other she was just another girl, so if she thought I was a pervert, so what. I later came to fall in love with her.

I think the mistakes a lot of guys make is to wait to long to reveal out little perversions. Once we are emotionally invested, we become afraid of telling our wife or significant other about our interest out of a fear of rejection. When you're up front about your perversions you have a much better chance of finding a good wife.

My then girl friend, now wife, took to it pretty much from the beginning. It just so happened that she had gone a long time without fucking any other guys when we started dating and after a few months our relationship became a long distance one. After she got used to getting it from me daily, going weeks without me was pretty hard on her. So I gave her the green light to fuck guys on the side, so long as she was honest with me. Our relationship over the next ten years has been that way.

She's free to fuck guys she's interested in on her own, usually guys she meets through work. If I suggest it, she'll fuck a guy or two off the internet.
torontoboy

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Posts: 20
#13 · Edited by: torontoboy
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I agree with you, it is a very exciting period. However, I know this is just the start. I feel extremely turned on when I think of the future possibilities. I'm not sure why I yearn for this, but I just do. We have both been completely open with each other (about everything but the most minute details -- more on that later). Last night she mentioned how she feels like she is very lucky to have found me. I already knew this in my heart, but she said it out loud: She promised me she'd be completely loyal to me, and that I would be her priority, but that she couldn't promise outright faithfulness. (To which I got an instant erection.) I told her that I would be completely monagamous to her and that I am not afraid of what the future may hold for us together as I know she would always be open about things and that we would discuss things.

Now for the juicy tidbit... Like I said you can be completely honest, but also still maintain some privacy. One doesn't need to give a complete report of everything that goes on in one's mind to the other... and on this note, I happened to use her laptop the other day to do a Google search while at her place. She seems to have the auto-fill form filling history thing on, as I typed the first few characters of my search in, other older searches popped up as options to auto-fill... One such search was (and I quote): "how to feel more when he has a small penis"

She has never outright said I have a small penis, partly because I was openly self-effacing about it all from the start, and I knew she has been with many larger guys (mostly, if not all -- since even the guy who was smaller at 4.5 or 5" by her best guess, she mentioned how he was freakishly thick) but there's always been the playful innuendo -- her way of telling me she knows I'm small, to which I playfully say "ouch" to.
torontoboy

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Posts: 20
#14 · Edited by: torontoboy
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Well, it happened. But not quite how I had envisioned it!

Things were getting downright domestic for a while, with her talking about moving away with me (I just got a job offer overseas), just as I was starting to get a little more stressed with finishing up a huge project at work, but also realising that I really didn't quite "feel it" for her in the same way she did for me (as in the future together). I told her I needed to focus on work and couldn't devote as much time for her as I had done earlier in the summer, and she took it fairly well. This was not technically a break up after all, just a cool off period due to work. However, there was still the odd romp here and there, up to the beginning of September.

She then started to get a little impatient with me and I brought up that I was not trying to tie her down, that she was free to do/see anyone she wanted. She then suggested a one-sided open relationship type of arrangement (i.e. cuckolding me, but without using that word). I have to say that despite my declining enthusiasm for the relationship (in retrospect, probably due to all the stress I was going through), this instantly turned me on, even though this was just an academic discussion over the phone. I gave her my blessing and left it at that for that night. Unfortunately she emailed back the next night saying that she realised that it was just a last ditch attempt on her part to somehow keep me in her life, that it would just be a sort of "game" to keep me interested/jealous, and not the cuckold fantasy that we had previously discussed, one which would develop after we had developed a stronger foundation together. I just thought "oh well", and just focussed on work from then on...

Until a few days ago, when I happened to click on a bookmark I had made of an old blog she had showed me months ago, documenting her past travels... It turns out that this blog had morphed from travel blog to sexual adventures blog! It seems she had joined some type of adult permisterals system as she felt she was in dire need to "break out" sexually. (Though, by my standards, she was already quite sexually experienced!)

Apparently, after a few near misses throughout September with a few guys (phone tag issues, weirdos) and chickening out from a threesome with a couple, she met one guy about ten days ago. Reading the post about their encounter made me instantly hard. She made reference to a "wonderboy" in the post, which I knew was me (she had used that nickname jokingly a few times in the past), and reading what she thought made my heart pound as hard and fast as if I had just run up the stairs. I guess this is a little like what true cuckolds must feel!

This is an excerpt from her blog post:

Overall the sex wasn't bad, much better than anything wonderboy ever attempted to conjure up and I wondered how I had even considered giving up on good sex just for a chance to live in a sexy city abroad. Thank god for big cocks I thought, and yes Virginia there is a Santa Claus!

We would fuck twice that night, although he went from hard to semi-hard at times and I was a little nervous myself. But we both left quite pleased. He would call the next day, and then ask to see me again the following night. Sex would be taken up another notch on our following rendez-vous and I had absolutely no reservations about letting wonderboy completely go from my thoughts at this point. Our conversations were still somewhat juvenile and he too often used the word "Wicked" and "Awesome" a little too much for my liking, but with a 8.5 inch cock, one can over look such frivilties.
for_fun_and_games

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Posts: 97
#15
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A girl always has to know you love her. If you don't or don't show it, she will walk. Sooner or later.

After all, in a cuck relationship you're allowing her to fuck other guys, so the sexual bond is different (if not weaker) than in regular relationships. Therefore, the emotional bond has to be that much stronger.

If it wasn't there, it was never gonna work. If it was, and you just got distracted, you fucked up. There are not a lot of girls suitable to this stuff.
Johnnyangplay

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#16 
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jamesriske
I don't think I've ever seen someone make such a good call.

Well stated.
http://indiecuckold.tumblr.com/
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Honesty is the best policy when meeting a new girl
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