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5
Pantypirate
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@confessions
06 Mar 2024 7:01PM
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Had the pleasure of stealing this hs girls dirty thong a while back. Just wanted to share this glorious pic of her ass she posted for all her friends to see. The things I would do to that ass..

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@confessions
03 Jul 2024 1:21AM
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I got married recently, to a long term boyfriend. A little back story - we were dating for 8 years, and since it was our time, as we are both pushing 40, we have done it.

Interestingly, he has began questioning me about my previous love life, and he has never done this before. He knows I had a long term bf for ten years, and my first bf in hs, but now, he is into specifics - asking me how he was like in bed, and similar yet strange questions.

I gave him crumbs, not going into specifics, and it got him super excited, and I must admit, elevated our sex life for a while. Now, he wants more, asking me to describe him the best sex I had with him, if we have done something weird etc.

I asked him back for his ex gfs, and that made him back up a bit - I saw he didnt feel quite comfortable talking about it, and he tried to slide with old "you are my second, there is nothing to tell", but after a while, he is at it again.

Now, my ex was a party freak, born rich, his life was an endless party, and in the end, that was the reason I left him - when you hit 30, you dont see the future with a man who is coked up or drunk all the time.

So, my 20s were wild, and on more than one occasion (but not often), I had sex with him, and his friend(s) after hard partying, and there are quite a few things to be told, but I am pretty sure my husband would freak out.

And the most peculiar part is - my husband is not a freak in bed, he is very timid. I once proposed (long time ago), that we might watch porn as a mean to fire us up - we did, and he asked me to stop, wasnt into it. In sex, I was always the one taking the lead towards new things, and always, but always, he would be reluctant about it, he almost looked scared of intimacy. This makes his newly developed interest more than strange.

I am in quite of a dilemma. My reason screams "dont do it", but on the other hand, since he is so horny and pushy, I want to open up a new frontier in our sex life, while at the same time, I almost want to hurt him for being so interested in it, by telling him about that one time, I sucked off my ex and two of his friends, or that time, I was fucked by him and one of his friends, on turns, for six hours, after two days of non stop partying.

I am not sure yet, but I am leaning towards the first option, to keep my mouth shut, since I am quite confident, that a man cant open up sexually, if he hadnt for 8 years of a relationship.

Am I wrong in presuming this?

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Anonymous
@confessions
17 Jan 2024 1:46PM
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I needed to drop my vehicle off for service today. So after I dropped it off I took a quick walk to a local Starbucks to get a cup of coffee while I wait. The Starbucks is small with not allot of seating so finding a good place to sit so I could plug in and get some work done was annoying.  Either way I was not able to find a good place to charge or able to tuck into a corner, so I just sat at the first open bench seat there was. While I was there for maybe an hour,  at least 10 HS ladies placed an order there. And man did I have a good seat. I was sitting in perfect view of all those perky tight asses standing in line. I could not help but stare and think how wet those holes must get. There was one girl who was on the bigger side. But she was wearing skin tight short shorts, and I could make out the out lining, she had a puffy one! I could not stop my dick from getting hard. I tried my best not to get caught staring.  Fuck I miss being at that point in time. 

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Anonymous
@confessions
08 Apr 2026 9:39AM
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My cock is on the smaller side so my girlfriend and I use toys sometimes to compensate.

She just told me today that the 7-8 inch dildo I’ve been using on her was made from a mold of her hs boyfriend’s cock.

im so conflicted and don’t know how to feel about it

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Anonymous
@confessions
23 May 2025 2:35AM
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Have you ever had a woman you wanted and lusted over for a long time, and then, when it finally happened, it was all you imagined it would be, only to be disappointed at the end?

We both knew Maya back in hs. She was by far the pretties girl in the entire school, but she wasn't popular, no, she was one of the nerdy girls, yet, the way she dressed, so closed and unrevealing, nor the way she acted, all shy and introverted, couldn't fool guys to look over her hotness.

She was our friend, and we both lusted over her. I tried something, she rejected me, like she rejected everyone - no one could touch her.

Now, this all happened in my home town, and as I went to college, she stayed, with him, my best friend. First Christmas I came back home from college, they already became an item, but we kept contact, all the way through college. Every time I visited, she evolved more and more, into a mesmerizing woman, being with him gave her confidence, both socially, and about the way she dressed, behaved.

I got married to a girl I met in college, in the city, after graduation, and they started living together, back home.

Twenty something years have passed. I got divorced in the mean time, and bought a little condo back home, for vacation, and started spending more time there. We lost touch over the years, but when I met him, and asked him about her, he confessed they broke up years ago. Then I bumped into her...

Saying that a 44 year old is stunning, always has to be taken with a bit of salt, but man, she was. I had no time to waste, texting have started, coffee dates, dinners... After one, she agreed to come back to my condo. When I kissed her, she kissed me back, and then surprised me, by going down on her knees, by herself, moments after, and unbuttoning my pants. When she took it in her mouth, I couldn't believe it. This was a woman, who I have been obsessed with for over two decades. I jerked off to the thought of her, thousands of times, and there she was.

It was wonderful, sensual, romantic. She came, while on top of me, tweeting like a little bird. Then I got to be on top, and when I was about to nut, I pulled out, but my excitement got the better of me, so instead of shooting for her belly, I unloaded all over her bald, perfect pussy.

"You didn't have to,"she commented,"there is no worries there".

That night, I learned that he left her, because she couldn't have kids. I also learned, that she is absolutely still and forever in love with him, and I decided, that that plot, is not healthy for me.

I did buckle, two more times, we spent two more nights together, before I packed my shit and got out of there, not to come back for another two years. She may be my perfect woman, but I am not her perfect man, and that would come back to bite me in the ass, sooner or later.

And that is my, said, love story.

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Anonymous
@confessions
07 Feb 2022 12:36AM
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I just want the world to know that I graduated hs over a decade ago and still rub my cock raw dreaming about ripping my language teachers asshole

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Anonymous
@confessions
28 Sep 2013 11:15PM
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hs and college homecoming time...thinking about the hotties getting their legs spread for the first time...should look around tomorrow for the walk of shame...or the smile on their face...lovin facebook pics of their homecoming dresses, hottest one ever was niece...wish i could find that pic again...mmmm

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Anonymous
@chicks
20 Mar 2013 9:14PM
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Some slut I knew from HS, she's a stripper now. I have one nude pic, she's legal.

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Anonymous
@chicks
28 Jan 2016 10:14AM
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Friend of my sister named Kati. She is a grade A slut. Senior in HS, just turned 18 in November.

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Anonymous
@confessions
22 Dec 2023 3:40AM
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I got divorced almost three years ago. I am a female, in my late 30s, and I have been married for 15 years, so I married young.

He was my first, if you dont count a few innocent hs pettings, and our sex life was pretty non existent, for the last few years of marriage. I have relived myself, many times, and eventually got sucked into the world of erotic forums, porn sites etc.

After we split up, my libido just jumped through the roof, and my online addiction sky rocketed. I wanted sex so badly, I have caught myself having these indecent thoughts about men around me, at work, at the supermarket etc.

Why didnt I do anything?

I am affraid. I have had sex with only one man in my life, and I guess I was insecure, so I stayed locked inside this cage I have built for myself.

Through all this, I started chatting with this man, some ten years younger than me, via this erotic forum. It became a form of hotting, with words at starters. Then I sent him some photos of me, without face and clothed, he sent me his, and he is a handsome, handsome man, so handsome, that I have wondered what such a good looking man is doing sexting a woman like me.

It evolved, i sent him some bikini photos, than partial nudes, and full nudes at the end, and eventually we saw each other on cam.

It was so sexy. He was raining down on me with compliments, throughout all of this, how beautifull I am, how hot I am, and such things are nice to hear. LIttle digression - I know I look good, and my looks werent the obstacle for me to find someone to have sex with - it was the other issues, I discussed earlier.

So we continued with this for more than 6 months, and it was hot, so intense. He was so good at describing things, it was like living through an audio version of the best erotic story ever written. Him, talking, made me climax every time, but looking at him through the camera didnt hurt either.

And he was obsessed with my behind, always asking for me to show it, and if I did, he would climax almost immediately. He would always tell me how he wants me from behind, or in a reverse cowgirl etc, and it got me appreciating that part of my body, and I did become aware that it does look good for a woman of my shape and size.

Long story short, after almost half of year of this, one day he sends me a message that he is coming to my country on business (we both live in Europe - different countries), and that he will be in such and such hotel, room number ..., and gives me his telephone number, for me to call him, so we could go out for dinner and, who knows.

I decided not to go, not to call him, it was all fun, but one thing is a fantasy through the weil of some anonymity, and this would be something completely different.

I was fighting myself on this one, I wanted to go, but I was scared, really scared that I will ruin it, by meeting him. You have got to understand, this was a kind of a relationship for me, something I was looking forward, seeing him online.

He was staying there for three nights. On the second night, I called him at 1 a.m. My voice was... I was scared. Asked him if I can come over to his room.

An hour later, I was there, in leather pants (god, what was I thinking), and a bottle of wine. We started going at each other immediately, we were both so desperate. He ripped my blouse off of me, and went for my breast right away. I was on fire, ready to go, like I have had hours of fore play.

And as we started to undress, I remembered his fixation, so as he was laying on his back, I got on top of him, kissed him, then turned the other way. I have never had sex in this position, so I was a bit scared, but ready to go. He had a condom on... And he came after no more than 20 seconds.

My dissapointment was inmesurable. He did try to get me off, afterwards, but wasnt good at it, so I faked it. I excused myself, and lied to him that I will see him again tomorrow, and told him it was good, it was all I was hoping for.

Never saw him again, not in real life, nor online. But this awkward experience was an eye opener of sorts. What was I affraid of?

Two weeks later, I met a man of my age, also divorced, like me, and I am having the best sex of my life.

I think this whole experience helped me understand a few things about myself. And one thing is for sure, I lost years of my life, living of sexual scraps, from my husband, later on, from online erotica, but nothing beats the real thing, when it is done right.

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@confessions
07 Sep 2012 11:05PM
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I really do enjoy the girls on here that are taboo, not because I would want to contact one the way some people post about. I was hurt as a kid and I wouldn't want to see that happen to strangers or close family. I just enjoy the ones that wanted to be exhibitionist with a body that will never be as artfully beautiful again in the same way. I love women of all ages. I can appreciate the much older women that still want to be the exhibitionist they have likely always been, all the way down the line to cougars, miles, college, HS.

But the less aged girls (grass on the field rule) are the ones you fell in love with when you hit that special time in a boys life when his imagination becomes his greatest friend and enemy. And to see them today is gratifying and exciting to that kid that most of us, hopefully, never let go of.

I just wish there was a good way for all parties involved to be properly compensated.

And to the morally righteous that surf a porn site, yes, I do feel very fucked up for coming here to peruse the photos I am referring to, but I felt fucked up for looking at any porn, just because we draw arbitrary lines in the sand doesn't make a person better than any other.

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Anonymous
@requests
21 Jan 2013 7:15PM
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Can someone try to fake this? or cum and repost? It's a girl I went to HS with. her face is kinda blah but her body is banginnn.

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razgledampomalo
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@confessions
19 Mar 2024 6:49AM
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I had this girl in hs, my first ever. She wasnt a beauty, but was cute, had big tits, and at that time, we had the most amazing sex I could imagine. Of course, after gaining some experience, I realized sex was shit, since we both were virgins, but it worked for us back then.

More than 20 years have passed, and we kept in touch through social media. She was married (I never was), and when I saw that she is alone now (she wasnt announcing it, I just figured by her online behavior), I started messaging her (a few months after I realized it), and we eventually met, like old friends.

It didnt take long to get back where we left off. I started cumming in her right away, she didnt object. I will marry this woman, just like that, after years of solitude. And the sex...

Oh man, I never knew a woman can be so experienced, yet so eager to please. She even proposed anal (I have never done it before), and we perform it once or twice a month.

I am in heaven.

So, chin up boys, good days might be just around the corner.

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@random
12 Jul 2024 2:05PM
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do you guys think i got prettier or uglier? left is me in hs right is me now

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@confessions
26 Feb 2025 2:45AM
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I have always been pretty free, regarding sex, which is self explanatory, since I am here.

I am in my 40's now, married, and my character is the reason, two friendships have ended.

I had a best friend, she was a blonde, as I still am (she went brunette in the mean time), and through hs and in our 20's, we spent lots of time together. She was my confidant, she knew all about me, how promiscuous I was, while she was the opposite. Hell, I envied her, for her looks, even though I never looked bad myself, and I had this desire to make her like me, to push her over the edge, so she can be like me, not just understand me.

At the time, she started dating, casually, this one guy, and she was opening up about their sex life, in a shy way, she always felt self conscious while talking about it, and just for laughs, I suggested we should have a prank of sort with him, when he comes to the bar, that we are both willing to do him, to see how he reacts. Why not, she just started dating him, she didn't really care about him, and she said yes.

We drank a lot, and, ended up at his place, on our knees, doing you know what, together. He fucked us both, and ended up unloading on my chest, I guess, because I have big ones, unlike her.

The morning after, I felt remorse. She broke it off with him, and we tried, and managed to overcome this, since it was obviously more than she could handle.

But, they got back together after few months, and things went cold. We tried hanging out together, but I don't know what it was, her being afraid that I might steal him, or something else, it didn't work, and we parted ways, while still keeping phone contact of sort.

That drove me crazy, so I started dating one of his friends. In hindsight, this wasn't thought through, especially since I ended up marrying him. My poor husband got ghosted by his friend, without even knowing what is it all about.

And that is it. I know this isn't anything hot nor super special, but if someone wants my unsolicited advice - do not mix your friendships with any kind of sexual activity.

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Anonymous
@confessions
11 Jun 2015 8:06PM
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My neighbors daughter just graduated hs. Been to parties with her drunk in a bikini and want to fuck her in every way. Help/advice. What would you do?

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Anonymous
@confessions
14 Oct 2012 3:42PM
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My brother and I played truth or dare - show me yours, show you mine kind of things. We gradually got more daring and started with dares leading to touching and sucking. Eventually we reached the point where we would just suck each other off without the pretext of truth or dare.

We weren't really gay, I don't think, and I have never done anything with another guy. We used to go through my mom's bras and panties to get turned on, which led to us trying them on. This gave us the idea that we could take turns pretending to be the girl with each other. Almost every night we would dress up and take turns sucking each other. When we reached HS, we went further and would have sex with each other. One of us being the girl by wear a bra and a wig. This went on through college and up to present day. It is a lot less frequent now that we're both married and have families.

Thanks for listening.

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Anonymous
@chicks
02 Dec 2025 12:29AM
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Former crush from hs was too cute. Need to be fucked

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Anonymous
@confessions
11 Dec 2024 2:32AM
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I had a best friend in hs, we were neighbors and inseparable. She was, and still is, one of the most beautiful women I have ever seen. Me, on the other hand, I am short, stubby, and far from being pretty. She always had the attention of men, our age, and older, but she was a kind of girl that didn't enjoy it, she tried to hide her body, introverted and waiting for someone special.

There was a man in her life, in senior year, he was our age, our class mate, but he seemed so mature. When a 19 year old talks about literature, and poetry, that strikes pretty hard at that age. He was all over her, but she didn't want any of it, but he was so persistent, that one night, she gave in, and lost her virginity to him. She told me that, the next morning, along with her decision not to stay with him, since, he is not the man for her.

I was always envious of her, and that made me want him, but I was too much of a coward to do anything about it. I remember thinking of him, almost every day, with a hand down my knickers, and that lasted the whole summer. Then, they both moved away for uni, and I was left behind.

Life went on, I met my now husband, lost my virginity to him at the ripe age of 21, but I continued to live in a fantasy world, lusting over men around me, and that fantasy, eventually is the reason I am here.

I met him few times after that, on the street, but the first time we had an opportunity to talk, was at our 20 year graduation aniversary. I was wearing I short dress, he told me that I look good, and a little after midnight, I was on top of him, in his car, cumming like there is no tomorrow. After that, he threw me on my back, and fucked me like I have never been fucked before, fast and hard, and he didn't bother to pull out.

It has been two and a half years since that night, and I still masturbate to the memory of it.

I know some might not find this very interesting, but my whole sexual life is in these few lines.

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Anonymous
@random
18 Aug 2025 4:56PM
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Which hs girl would you fuck?

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@chicks
01 Oct 2014 11:11PM
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girl from HS

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@confessions
14 May 2022 3:47AM
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You know how we all had that girl we lusted over in hs? Usually, it was the hottest girl, and you had 0 chances with her. Well, not for me. I was into this quiet, petite girl, and she always wore saggy clothes, and never was into the crowd and stuff, but man, she was, and still is, the most beautifull woman I have ever seen. Brunette, big, big eyes, luscious lips. Man, I am telling you, she was out of this world.

May is the time of year in which, there are aniversary celebrations, of graduation. 20 years for me. Last weekend I was there. In the mean time, I have been doing well in life, but she hasnt. She is still beautifull, dont get me wrong, still the most beautifull woman I have ever seen, but, judging by her clothes and, you know, lack of anti age treatment, you could see she is not in the best place.

She married some bum. Not literaly a bum, but a guy with no future, and she lingers on. We started talking, and she was really into learning about my life, since I moved away from my home town after graduation. At one point, when we were already pretty drunk, she told something like "ah you forgot about all of us, this is like a visit to a previous life for you", at which I blurred that I will never forget her, and that I never had.

That got her interested, so she was persistant. I admitted my infatuation with her, back in hs, and that I have thought about her many times after graduation. And that she is the most beautifull woman I have ever seen, and that I still have a boyish crush on her.

I guess she needed a compliment, or something like that. An hour later, my cock was in her ass, and I was dirty talking the most obscene shit you can imagine.

Life is good sometimes.

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@confessions
06 May 2024 6:21AM
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I am 41, have never been married, and my sex life kind a went to shit after I hit 35, so, occasionally I end up here.

This is my confession, it aint much, but it took me some courage to do this.

After I hit 35, my sex life died in a way. I was never beautiful, nor hot, but I did attract men, with no problem. Now, the men that want me are questionable, to say the least, and I am spending my time mostly alone. I have had a few flings, and one night stands, but regretted it every single time. I had a long term relationship which I threw away, over a stupidity, and now I am regretting it.

It may sound stupid, but I was with him for 7 years, and when the time came to talk about marriage, I realized that I had only two orgasms with him, for all that time. Going back, I was unsatisfied in two other relationships I had prior to him, in a similar way.

Then, it dawned on me - my first boyfriend ruined me.

We were seniors in hs, and he had prior been with this girl, everyone envied. When he showed interest in me, I was over the moon. We proceeded having a year long relationship, in which, he was more than dominant, sexually. Now, when I think of it, it is strange for someone who is 19, to have such confidence, and such kinks. He was my first, so I didnt second guess it, but I was cumming hard, when he choked me, slapped me around, called me names, he would even cum in my glass of water, and make me drink it during breakfast...

After we broke up, and I met my next bf, I realized how insane our thing was, and I was angry, felt betrayed and disgusted by myself, for letting someone treat me that way.

But, him, the next guy, and my not destined future husband, all were so gentle, and vanilla, and respectful to me. Yet, they didnt make me cum.

So he broke me. Made sex for me, being, degrading and hurtful, as the only way I could get off, but on the other side, I do not want to feel the way I felt with him, but I want the orgasms he gave me.

So, I am nowhere.

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@confessions
10 Mar 2025 8:54AM
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Goonin to Katie so much like a pathetic loser, been obsessed with her since HS
i miss her 

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@chicks
31 Oct 2024 8:11PM
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Comment if you'd rather fuck petite Mari (left) or busty Abby (right) and I'll comment a sexy pic of them. The pics of Mari are from when she just turned 18 in hs and the pics of Abby are from her slutty college days.

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@confessions
08 Aug 2022 4:55PM
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So to start off I'm 24 year old female living back at home with my parents after just finishing college this past Spring. Living with mom and Dad and my younger brother who will be in his last year of HS. I'm a bit of a slut who is into everything really. Guys, Girls, bondage, S&M, etc. I lost my virginity when I was very young to a boy who was 5 years older, although, I lied about my age, because, well, he probably never would have touched me otherwise. Since then, I've been with over 25 different guys, 12 girls, multiple threesomes and one sort-of-gangbang. I say Sort-of, because it was really just 5 different guys taking turns on my ass. I wanted to see how much cum I could take in my ass before I started to feel cramped. For the record, it's 7 times. (Again, sorry to Paul for blowing out all that cum on him...I couldn't hold it anymore! LOL)

Anyways, my room is a converted attic bedroom smack dab in the middle of the house. Directly below my bedroom is an office we all kind of use, and part of my brothers room. There is a hole....

I don't know why i am giving all these details..the jist of this is that I want to suck my brothers dick! I've seen him naked many times and he's in incredible shape, and has a cock of a porn star. Easily 8-9" long. He strokes it with 2 hands for fucks sake! I have watched him masturbate many times. One time, I licked and sucked the cum out of a rag I saw him cum in and then toss in his garbage! It was fucking delicious!

I've started walking around the house in my bikini and sun bathing topless (face down) and noticed him checking me out. Even going so far to invite his friends over to swim knowing I'd be out there. I can't prove it, but I am certain he took a pic of me and jerks off to it. I'm doing this to try and see how he feels sexually towards me and if he would let me suck him off.

I told one of my friends about this strange little fantasy of mine, and she said, I should just ask him if I can suck his dick! I think that may be taking things too far. I told her that we should set up some glory hole thing and have him think my friend is going to blow him, but I really do it.

Advice? Do you think he would flip out? Tell our parents?
I just want to suck and swallow him, not fuck him. well, maybe not fuck him...gawd, I don't know!
I just know I want what i want.

What do you think I should do?

Maybe just move out and put these thoughts out of my head!

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@confessions
24 Jun 2023 3:56AM
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Last night I had a 20 year HS reunion. Got a bj from a woman who was my crush, and so out of my league back then. She never got married, and last night she swallowed.

My confession is, that I felt a little disgusted by her.

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@confessions
01 Mar 2014 10:07AM
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So idk what to do. Me and my gf (first pic) are getting kinda dull in bed. After 4 years of the same pussy it's hard to last long she isn't tight as before. She has an amazing fat ass I'll admit and she's thick. Lately her hs friend that goes to UofI Champaign has been snap chatting me at first we would just be bored and send goofy pics then we started flirting a lil. Yesterday night she finally sends me this pic. It's been a long 4 years since I been with a tight slender girl n I wanna feel her tight pussy. She wants me to go to Unofficial next weekend (3 day long party to celebrate St. Patricks day early) and she wants me to stay at her dorm. Here's the crazy part tho. She knows my gf n knows I would have to bring her, so she wants to just get her drunk until she knocks out so we could fuck. I'm not sure if it's worth it I got until Friday to decide.


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@confessions
07 Jan 2025 3:04PM
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So, the wife had an online thing going for a little bit with a guy. We share each other and are both ok with one being with another. We have to though let each other in on anything that goes on with the other person, conversations, calls, texts etc.

She'd been talking for a bit with a married guy off and on. We weren't sure if it was going to be a full-on swap, or what was going to come out of it, so we just rolled with it. Turns out he'd been married to his wife; she didn't know about him going outside their marriage and talking to others but found out. She then after some time had passed, she gave him a hall pass as he gave her one too. So, after many more weeks to near a month of planning and arranging, we were able to get him out here with us. For what we all understood as a textbook cuckold experience. I watch him fuck my wife (which the wife and I did a lot). There was, once all parties were aware of each other, full communication between all four spouses. His wife did confirm that she was his first as was he for her and that they have been up to that point the only one they'd both been with. They were HS sweethearts.

So, the day came when he was to get here, and he was a decent looking guy in person. You can never really tell with pics with the filters and such. But he was sort of fit but working on it. Had a what my wife said beautiful cock. The night of the arrangement, he got to the house. We brought him in for our first meeting and conversation to ease the tension. Chit chat went back and forth. One of the questions the wife jokingly asked him was is he excited to have sex with his second woman ever. He was beyond excited. He did prior get full testing done and provided us with the results. So, we and his wife were ok with him not using a condom.

We slowly went to the bedroom. I assumed my position in the corner sitting in my chair. Wife told me to take my clothes off so she can ensure that I had my cock locked and not able to get hard. Their activities continued on the bed, her clothes started coming off, as did his. He went down on my wife to start with, his cock you could tell was already ROCK hard. Few minutes of him licking, wife took control of him and flipped him on his back and went down on him. She was doing great work with her mouth as she usually does with her dates, you could really tell he was enjoying it a lot.

Oral activities ceased and she rolled back on to her back and he got above her, missionary position. Now came the moment. He was between her spread legs, grabbed the base of his 7-inch cock and pointed it toward my wife's vagina so he could enter only his second vagina ever with his condomless cock. The tip was at her entrance, in one very slow thrust his head disappeared in her, next thrust about half his cock disappeared in her, with the third thrust his bare super hard cock was fully in only his second vagina EVER. A second thrust as he pulls out you can see my wife's juices all over his cock and then again, he disappears inside her with his slow steady thrust. Third time, he pulls out and he swiftly pushes it back in quickly and this time he went balls deep in my wife. Now he held it and let out a huge moan. He was, after just entering his second vagina ever, blowing his load after three pumps in my wife's pussy. Only thing visible was his balls as he pumped his load in her as deep as he could go.

Having now done what he's only ever done in one woman before, he withdrew his now semi hard cock. His tip would twitch every few seconds and he was still leaking a few drips from his cock. I just couldn't he said looking at us both. I just couldn't stop it, it felt so amazing I just couldn't stop it. I didn't mean to cum that fast. Wife looks at him and tells him it is ok.

She then has him reposition himself up by her mouth so she can suck his cock to get him hard again. Just before she takes him in her mouth, she looks over at me and says clean up this mess. So, I do as I am told, put my face between my wife's spread legs and proceed to clean and swallow her dates fresh load as she used her oral skills to get him hard again.

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@chicks
07 Sep 2025 7:00PM
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Who would fill Marissas holes deep hs slut

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@chicks
22 Oct 2023 12:17AM
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Hs grad 2023 what you think teachers say

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@confessions
22 Dec 2020 9:16AM
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Confession...I haven't had any kind of of physical contact with a girl in 8 years. None. This is after having an extremely active sex life from HS up til 8 years ago. In that time, I've had sex (intercourse) with over 100 girls and at least kissed/done everything but f'd countless more (hundreds). I don't mean to sound like someone high on themself, but it's the truth. For a while I could get any girl I wanted...I did it all. Then, it came to a screeching halt. All to nothing. I had all the confidence and pussy I wanted. Now? My confidence is shot and I'm doubtful I'll ever even so much as kiss another woman again. I treated many of them like shot so I guess karma has really taken me down.

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@confessions
13 Sep 2012 11:59AM
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I like eating my wife's ass. However, there's a little gymnast student in my HS chemistry class who shows off those shapely, strong little legs in tiny pleated skirts. I'd like her to kick the panties off as I lay back on the big demo desk. She can squat over my face and lower her gaping shithole over my probing tongue as I run hands roughly over the rippling muscles of her thighs and ass. Then grip my tongue with her squeezing anus and yank on it as her clit rides the point of my chin on Mondays, and the tip of my nose on Wednesdays. She often has strange, sticky marks on her papers when I hand them back to class.

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17 Jun 2023 2:49PM
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Hs

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@confessions
21 Mar 2024 2:46AM
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You know the feeling when you strike gold on the first try? Well, I know it now.

Little back story, I am close to 50, married, and my life was good, and happy. Have a nice family, and everything seems to go the right way.

I had a few girls, women, and I can say my sex life was interesting, I might say above average. But I have this, "what if", question in my mind.

My first real gf was my hs sweet heart, and I often think about her. I did love her, but it is not about that. We had the most amazing sex. We were both virgins when we started dating, so we learned along the way, and were both eager to do more, explore, we werent ashamed of each other, since we were both blank pieces of canvas. I never had anal after her, never had public sex after her, never had a woman dress up and role play like she did.

It has been almost 30 years since we parted ways, and I still think about her, and I think, how would those 30 years look like, if we never broke up.

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@confessions
06 Mar 2024 5:22AM
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This isnt much, but here it goes.

I was married twice, and recently ended my 2nd marriage. I work long hours, and it seems that both of my ex husbands didnt like that, probably along with the fact that in both cases, I made much more money than they did.

And, funny thing is, that those were the only two lovers I had in my life, married my hs boyfriend, and after I divorced him, married a colleague, and that is it.

Now, I am involved with an older man (I am 43, he is 50), and the thing is, sex is different. He never tells me to turn over, he turns me over, he calls me names during sex, cums on my hair, slaps me etc.

Reason I am here is because I always felt that I should explore the darker side of my sexuality, and I guess I was right. I had more orgasms in three months with this man, then I did in 12 years of combined marriages.

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26 Oct 2011 12:11PM
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Any tips on how to get a girl?

I have never had a girlfriend before and recently moved from England to the US. Despite being a bit of a nerd with absolutely no confidence in the dating department who spends most his time jerking off to porn I decided that my relocation to America would be the perfect opportunity to reinvent myself.

Thankfully I am very good at football (soccer) and so joined my HS soccer team which allowed me to make friends with all the jock types and in the past few weeks I have become a bit of a star player for the team. A group of girls always come along to soccer practice and watch. I think one of them is really hot and we have been talking a lot over facebook. Normally every night. She always drops hints like "I think the British accent is really hot" and "You seem to be popular with the girls", so I think I have at least some chance of getting with her.

My problem is, how do I play it? How do I ask her out? If I manage to get a date with her how long before I kiss her? If by some miracle we have sex, how do I make sure she wants more? Do I admit I am a virgin?

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@chicks
01 Sep 2024 7:27AM
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Here's to the guy that wanted to put a baby inside his HS heartbreak couldn't post this on time, have fun jacking off all night buddy

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@confessions
17 Feb 2025 7:54AM
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I am an introvert, and this ruined my sex life.

I have discovered, pretty late in life, that my looks are above average. Men in hs were interested in me, but since I was a weird girl, who stayed to herself, I guess no one dared to come forward. And there were these two guys, maybe the main reason.

I didn't fancy neither of them, but I fancied both, if you understand. One was a brute, who always got into trouble, a proper man's man, the other, much more handsome, well read, and they were both inseparable, but at one point they started hanging out with me and my only friend. They wanted something, but didn't really hit on me.

Now, to understand this further, you have to understand how my brain work(s)(ed). At that time, when my friend lost her virginity, I decided to do it to, but I couldn't with someone I knew, so I organized a rendez vous, with an older man. It was awful, but I did it.

I am same today, I have been reading these boards for over five or six years, and this is the first time I am writing something.

My only friend, lost her virginity to one of those two, the handsome one, lets call him M. They hooked up a few more times, and as she told me all about it, I was surprised that someone of his age, could be so free in these things, and obviously experienced. So I started to wonder about him.

The time for him to move out to college was fast approaching, and he was always looking at me, joking, but never made a move, and I was too scared to do it. The night before he was set to departure, I wanted to escort him home, and I wanted to make my desperate move, but I couldn't. I guess he saw that, kissed me on the lips, for goodbye, and got home.

Three days later, I hooked up with S, the brute, and we stayed in a relationship for 15 years, before it ended, he was to much of a maverick, fights, problems with the law, couldn't keep a job, etc.

I spent years pondering about my ways. M visits very rarely, and when he does, it is with his gorgeous blonde wife, and perfect kids. Hi just says hi on the street, not knowing that I have been thinking of him for the past 20 years. At the same time, me and S, hooked up from time to time, just to release our urges, we even tried to make up, but it didn't work.

So, that is my sex life, online lover as my first, one of two loves of my life, as my second, and the third was this insane idea I had, to have sex with two men, who would role play them. I set it up, online, didn't end well, they treated me as non human, double penetration is hurtful, not enjoyable, and their semen tasted like beer and ashtrays.

So I am in a celibate now, unless M comes back, but I know he never will.

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@confessions
15 Sep 2012 11:39PM
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So, I posted an ad on a Wednesday for here my parents live that I was looking for a couple to try a threesome. A lot of couples responded which floored me because where my parents live is a bit conservative. After talking all day from Wednesday til Saturday evening I realized this couple was the one I was going to agree to be with. They understood my rules and I theirs and it wasn't pushy.

Saturday night I had plans to go meet up w some old friends from HS and have drinks. After a few I told them I needed to go bc I was heading home early the next day. I'd already gotten a text from both the husband telling me he was hot to see me naked and from the wife telling me she couldn't wait to taste me, so naturally I was ready to leave ASAP. The husband text me the hotel room number and asked me to text once I was on my way. I text him back bc of course when I get there, there wasn't parking where he told me to park (near the room)

His wife comes out of the hotel and finds me in the parking lot, she doesn't have a bra on and I can see her nipples which made me a little wetter. As we come into the room he stands and hugs me and asks of he can pour me a drink. I told him I was fine as I sat on the bed. He gets up and makes his wife and himself a drink. After she takes a sip she sits next to me and starts kissing me. I can't help myself and I reach under her shirt and start rubbing her breasts and pinching her nipples. She stands and pulls my shirt off as I kick of my shoes. Her husband tells me how beautiful I look w my hair cascading down around my breasts. She leans me back and really starts making out w me. She has my bra undone and off in no time.

She starts kissing down my neck and stomach as she is undoing my jeans and starts sliding my jeans and panties off. When she slides her hand down to touch my pussy she murmurs how smooth it feels. He audibly gasps as she kisses my inner thigh. She starts eating me and he walks over and just reaches down and fondles my breasts then sits back down. When she stands she has her clothes off and I pull her onto the bed. She kinda laughs and says she wants to taste me as I get my first taste of her. I didn't think much about it but she had her head at the edge of the bed and my knees were barely on the bed. I hear him unzip his pants. He asks his wife if I taste as good as I look, she agrees and as she slides a finger in we both cum at the same time. We both kept going. I suddenly feel him rubbing my ass. And next thing I know her fingers are replaced w a hard slam of his cock filling me to the hilt. I cum instantly and she does too. Now she won't let me eat her anymore but keeps eating me while he keeps pumping into me and all I can do is moan and enjoy the sensations.

Suddenly she rolls me over, he kisses her briefly, tells her he wants to taste and next thing I know he's eating me and she's licking and sucking on my nipples. After I cum again he's back up pumping into me while she keeps up her attention on my tits and starts rubbing my clit. Her husband fingers her and I grope at her breasts. After I cum again he has her suck my cum from his cock and bends her over and starts pounding into her while she goes back to eating me. We all three came again together and took a bit of a breather. As we laid there him in the middle he took his time to make out with both of us. Next thing I know we'd all dozed off.

I woke up to him playing with a nipple and him kissing my neck which resulted in me pushing my ass against his already hard cock. Then I notice his wife is softly snoring. As he reaches down to start rubbing my clit he slides in while spooning me. It was a slow and sensual fuck that was so much more erotic bc she was next to us asleep. He kept fucking and rubbing, he'd doze off, I dozed off and as I'd move he'd start in earnest again fucking me. After an hour or two he finally rolled over and had me ride him until we were both spent.

I still talk to them and next chance I get when at my parents I will be having a repeat sex a thon!!

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26 Jul 2023 3:18PM
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Why does young Andrea always get deleted lol I know you guys would have some fun with her ;) especially with her looking like this right out of HS

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@confessions
07 Aug 2013 1:57AM
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At the beginning of last month I made a post about my first peeping tom experience.. I'm visiting a family member who's got a HS aged neighbor with poor window drapes, and who has a tendency to get undressed in front of said window, shortly before bedtime. Sadly, I still can't provide proof, but I finally got a real view tonight via a cheap set of binoculars!

I'll describe her again and more fully.. I'd say about 5'1, 95lbs & of some kinda Spanish descent, with long, bushy, curly black hair. (usually wears a bandanna in it, "Spanish style", lol) Due to the size of her frame, I'd say she's probably got solid B-cups, which looked like perky C's tonight/unclothed.

I have a feeling she may have rubbed one out while I was peeping too, but unfortunately the window's above my viewing angle/on a 2nd floor. She went in her room, speedily peeled her clothes off (didn't get the binoculars up in time, heh), and got directly in bed, but left the main light on. After 5-10min I was getting ready to put the binoculars down for good when she got back outta bed naked, put on a big nightshirt & dimmed the lights. (which went out for good shortly thereafter) A ritual that seems to happen often. Too bad I can't get closer, a better angle, take pics with the binoculars, and/or can't currently afford a better set! When I come back next summer I'll try & have a decent zoom lens, haha. (sorry again for no pics :( ) Will be sad when I go home, as there's nobody to spy on. Now I've got extra incentive to visit Grammy/come back though, LOL! :P

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29 Sep 2024 4:27AM
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Did you ever have a role model in life, someone you look up to, and who makes you jealous?

I did.

In hs, I had this friend, popular blonde, very beautiful, and she was my best friend, and still is, to this day, but she is not the one - her older sister. Also a blonde, very beautiful, but since she is two years older than us, I always wanted to be like her, to attract men she does, to dress the way she does, act and conduct myself, like she does.

I wanted to be her.

By all objective standards, I do look good, some would argue very good, but I always felt that I came too short, comparing to her.

All this, pretty much ruined my sex life. My bfs were all, not good enough, since I couldn't imagine that she would be with them. Later on in life, all this is responsible for thousands of dollars, I left to my therapist, trying to get rid of this infatuation with her.

First stupid thing I did, was to have sex with her college bf. We had sex in his car. She somehow found out about his affair, and dumped him. I was 100% sure she knew it was me, but no, he actually had no idea that we were friends.

While we did it, I felt like her, and it gave me the best orgasm in my life.

After that, since, you figured out by now that we stayed close after hs and college (I was a maid of honor on her sister's wedding), she started dating this big guy, and it looked pretty serious. But men will be men, and after just a few signs I threw his way, he made his advance. We had sex for over a year. That was a great time, and the sex was amazing, once again. We did everything, anal, dress up, role play, everything. But, the catch was, that after a year or so, he told me he wants to leave her, for me.

That was the best feeling in the world, but... I panicked, and just cut any ties with him. Once again, I thought she will find out. No, he just left her, without any explanation.

That is the point in which I started therapy, and after some while, managed to distance myself from all that craziness. In the mean time, she met a man she later married.

I evaded her, and everything around her, until their wedding day. He was dreamy - tall, handsome, successful.

That day, I hooked up with the best man, just because he was his best friend, and it turned into a relationship.

For seven years, I was with this man, and I was thinking of another. That sent me into a spiral of sexual deviance (I am here, am I), and fantasy. Since he was his best friend, and I was a good friend of hers, we started spending lots of time together. I didn't wanna do anything, not even try - special thanks to my therapist - but it was just pouring out of me. We would go to vacations together, and I would, for instance ,sunbathe topless, in front of them, even though I never did that before. I would wait for the right moment, to ask him, when we were left alone, to rub in some sunscreen on me. Besides vacation, I would do similar stuff, just to point his attention towards me. He didn't even look at me, I was totally uninteresting to him.

After our evenings together, we would go home and have the greatest sex ever, all because I was thinking of him, while being with my bf. After a while, I even introduced a dildo in our sex, I was riding it, while sucking him off, or sucking it, while my bf fucked me, imagining that he was with us.

Somewhere along the way, in therapy, we realized that I have shifted my obsession from her, to him, fully. I started detesting her, hating her, with all the bad things going through my mind.

Then, one evening, he told all of us that he has some problems at work, and that he can't find a trustworthy assistant. Without thinking, I offered myself. Everyone loved the idea - who can he trust, if not one of his wife's closest friends.

Maybe a month after I started working for him, I dumped my bf. It was just me and him, all day long, my time is coming.

Only it didn't. I did all I could, wearing a short skirt, showing a glimpse of garters, only to be warned that I must dress more formally. Same happened with wearing no bra on a white shirt - not professional. I gave my best, but he just wasn't interested.

This went on for years, and years, and my sex life was non existent, residing on the web of fantasies, I was living off.

I met a man, from a nearby town, with whom I started having casual sex, and, I ended up pregnant. I found out early, two weeks in. Told him, and he asked me to move in with him, asking me to marry him. I said yes, without thinking, but after further insight by my therapist, we all agreed, it was the only way for me to heal, and that that would be possible only if I go as far as possible, and cut all of them out of my life.

I have announced the news to them, gave in my two weeks notice, and they were both happy for me. She asked me to promise that we won't become strangers, and that we will visit each other.

The last day in the office, he stayed late, so did I. When I entered his office, he was surprised that I haven't left sooner, and I said something like "not without saying goodbye".

He stood up to hug me, and I kissed him. He backed off, surprised, but when I tried it again, he did the same.

Couldn't beleive it! After all the bending over, teasing, unbuttoned shirts, he didn't even get it. I grabbed his crotch, and he was hard as hell, so I just got on my knees, and started unbuttoning him. I didn't plan on kissing him, it just happened, but this, in my crazy logic, I wanted to leave him no choice, because, what man would refuse that from a beautiful woman.

He was holding one of my hands, but I put his cock in my mouth. He said something like, "no, please", but then I started thrusting hard, swallowing it all. At that point he gave in, and enjoyed.

I was so wet, I thought I would leave a puddle on the floor. It was surreal. When he came in my mouth, I swear to God, I came, handsfree, fully dressed.

He looked like he got tossed around by a hurricane.

"What a hell was this?"he finally asked.
"Nothing you should worry about, I am moving and getting married."

And that was the end of it. Two days later, we moved, and I never saw them again. It has been more than five years. She called me a couple of times, but I didn't answer, and after a while she got the message.

I have healed. This confession is kind of a burden dumping, since I can't tell this to anyone else, except my new therapist. I still have leftovers from that life, I visit this place, and there is a dildo in our bed room, but his face is not there any more.

I understand that this can be a bit overwhelming, but it is what it is. You can judge me, I get that, many poor choices are behind me, but are we even human, if we have none of those.

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@confessions
22 Nov 2024 3:20AM
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I got recently divorced, and last week I went on my very first date in 15 years. She is a bit younger than me, pretty hot, in her early 40's, never been married, and the date went well, she invited me to her place, and we fooled around, it ended in a very nice, and sensual hand job, and I am happy.

I tried to make more of it, went for her buttons, she backed off with a smile and words "not yet", while continuing to kiss me, and touch me, like she is the horniest woman in the world.

Since I have been off the dating scene for a while, this confused me in a way. Is this something that happens nowadays? I mean, last hand job I got from a woman, after a date, was back in hs. She seems to like me, we are going out again on Saturday, but I am not sure, if this time, I should push for more, immediately, or go with the flow.

This may sound stupid, but I feel more insecure now, than I did when I started dating, as a teen. What do you think?

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@chicks
26 Jul 2021 2:21AM
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Jordan looks so hot - she is very religious though. She went to the same hs as my wife but I would love to still have some fun with her.

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Pantypirate
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@confessions
06 Jan 2024 2:32PM
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How you guys like this hs senior in red? Can yall believe she’s already wearing g strings? I scored one of her worn ones

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@chicks
09 Oct 2023 8:24PM
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Damn hs girls no adays wow

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@chicks
03 Oct 2025 9:18PM
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Who would breed this tight hs slut 

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@chicks
11 Jun 2024 9:02AM
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What do you think of my old HS fling. Should I expose her info? What would you even want

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@requests
12 Feb 2013 4:26PM
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more of her. name is gina c. from long island. help me find more. also any girls from st anthonys hs would be appreciated

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@confessions
24 Aug 2013 3:56AM
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I want to confess that I lost my virginity to a much older married man and not my boyfriend. I am a senior in HS Yes I'm 18 and legal. I wanted it to be with my boyfriend but it didn't turn out that way. My boyfriend doesn't know and him and I have had sex since and he believed that he was the first guy to sleep with me. I don't want to hurt his feelings so I will just let him believe that he took my virginity. Is that wrong? I know I'm not going to marry him. Both of us are going away to college next year and we will be 1500 miles apart. Any ways I now realize that I am attracted to guys who are much older than me. When I say older I mean like 30s and up not 20 something's. When I'm out at the mall or whereever I look at older men and think what it would be like with them. Sex is ok with my boyfriend. But I find Im missing something more. I just don't get into it like I think I should. When i was with the older guy he kept calling me baby and I was calling him daddy which really got him and I going. I keep thinking of older guys when we do it. I talk with my girl friends and tell them my interest and one of my friends says its probably because my parents are divorced. I don't see my dad all that much maybe 4 times a year as he lives out of state. When I had sex with the older guy it was OMG so good! I cummed twice with him and I think about it all the time. He seemed to know everything I liked and paid a lot of attention to me more than me doing things to him. I want to hook up again with him but he is married. Are all older guys better with experience? I cant wait to go to college next year. I plan on trying to meet more older guys.

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@chicks
12 Sep 2017 1:07AM
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How would you use this hs girl? Was a friend of mine... got more if there's a want to see some more

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