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The Caught Compilation 21

The Caught Compilation 21

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Anorexic Butthole Destroyed by BBC

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Sexual Fatalities From Japanese Cartoons

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Anonymous
@confessions
19 Jan 2025 5:07AM
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Last night I had my first cuckold experience, and it is not what you think.

I am a man, born 44 years ago, never been married, and since I am here, you can guess I am a bit of a pervert. I was always looking for unorthodox sex, and that might be one of the reasons I stayed single, first because, I tend to push things fast and without thinking, which scared quite a few women off, and secondly, because in instances in which I found a woman who was open to many things, I went so far, that even she got scared away, after a while.

So, I dwell here, and in similar places. I take good care of myself, and I look superior to other men my age, and I could thank my genetics, along with the gym and track, but before mentioned has been a ballast in my love life.

So, I mostly chat, and sext with women online, had quite a few hot cam sessions, but I didn't meet any of them, except for one chubby, years ago, and that ended up as nothing more than a groping session.

Now, you can imagine my reserve, when this couple I was chatting with, on a local dating site, proposed cam play. It was nice, they looked really good, especially her. Around 40, as I later learned, brunette, very beautiful, a little bottom heavy, but still very hot. We did these cam sessions, weekly, for over three or four months. In that period of time, we talked a lot, I made her laugh, and it wasn't just this game of mutual sexual arousal, I could see they liked me.

She was the one to propose us meeting up, and through cam, it seemed that he was surprised by this. Our conversation ended quickly after that, but they were online tomorrow, and, they wanted to meet.

In person, I was blown away by her appearance, she looked like a real fine lady, well dressed, him as well, and I felt comfortable around them, and I could see, half way through our lunch, that they felt the same way about me.

Nothing happened that day, except we exchanged our phone numbers (me and him), and we continued our online sessions. He would text me, that they are talking about me being with her, while he watches, since it has been something they talked about before, and I used that to drop that seed in our chat. It was going on slowly, but one could see that the idea, now palpable, started to grow on her.

We went on another lunch, and drank, and laughed, and joked about it, and again, we each went our way, but it was a progress.

Finally, somewhere before New Year's, they said they want to try it, at my place, since they have kids. I agreed, but since I was out of the country, I just proposed that we push this meeting after the 15th, when I got back, and we agreed, this Saturday.

I thought a lot about it, figuring, they will chicken out, since they had so much time to think about it, but they didn't.

I have had, I could say, a pretty extensive experience, sexually, and my age would suggest that nothing can move me, or scare me, but I felt pretty intense waiting for them. I was afraid of so many things, how to approach this, and not to be pushy, how to set up the place. It turned out, that I was overthinking.

She was wearing this shorts, that looks like a short skirt at the front, with nylons, and boots. Instant erection. We had a few glasses of wine, before I made my move, touching her. We agreed on no kissing, but she was the one who leaned towards me. We were on the bed in matter of seconds, she pulled her bottoms down, and I just started eating her.

He was somewhere behind me, I could see, that she was looking his way, with a smile on her face, but I felt insecurity in her eyes. When she started cumming, she looked at me, before closing her eyes, and arching her back.

I got up, got undressed, and I wanted her to suck me, oh boy, did I want those lips on my cock, but she pulled me towards her, and pushed me on my back. We agreed on condoms, but there she was, on top of me, sliding down on my cock, raw.

I licked her hanging tits, her hard nipples, and she was riding me like there is no tomorrow. At some point, when she turned to look back at him, only then I noticed him behind her, standing, and wanking. I started touching her ass, rubbing the asshole with my finger tips, and then spreading her cheeks wide open, inviting him to join. And she was ready, believe me, even if she never let him touch her asshole, at that moment, she would take him with immense pleasure. But no, he just started cumming, all over my floor.

That was the last time I looked at him, and focused on her. She came for the second time, and I was so close, that I said it. "Please don't cum in me", she asked, without breath.

I wanted to get her up, cum on her face, or tits, in front of her husband, but in this fit of sex crazed rage, I pushed myself over the edge, so I just managed to pull out, and cum all over her ass.

When we came to our senses, we realized that he is gone. She started to panic, got dressed, and stormed out.

I checked the place, even though I keep nothing of value, no, they weren't thieves. They told me that it was their first time doing something like this, which I doubted, by the way she behaved last night, but I guess the weren't lying, and that post nut clarity hit him hard.

Texted him this morning, asking, if everything is ok. No response.

I guess that is it, but I wish I am wrong.

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Anonymous
@confessions
15 Dec 2024 5:23AM
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I had a strange relationship with my room mate, back in my 20's.

I just started working in the city, and she was a friend of a friend, who needed a room mate, so that is how we started living together. We were both in mid 20's, and she was this petite, beautiful brunette, very slim, flat chested, but with a great, athletic figure.

She was a great room mate, nice, calm, not too loud, didn't party, nor have people over, and I was pretty much the same. Of course she attracted me sexually, but I wasn't doing anything about it for two reasons, first one, not to ruin a perfectly well organized living situation, second, I figured she was out of my league.

It was a small, one bedroom apartment, so in the beginning I was sleeping on the couch in the living room. After a while, we figured that we like spending time together in the evenings, watching TV, and drinking cheap beer and wine.

In the end, she called me to sleep in the bedroom, since it had two beds, with an agreement that one of us will evacuate to the couch, if the other brings someone in.

That never happened to me, and she wasn't very active either, she had one bf, for a short time, but I think he slept over two or three times.

Neither of us had many friends, so it was just me and her.

She started going out of the shower just in her underwear, changed in front of me (never going naked, but stripping down to her undies), and I would joke about it, asking her to stop, since I haven't had a girlfriend in ages, and she was replying with some motivational shit, like, go out more, laughing it off.

I would use this new situation, to go out of the shower just in my boxers, with my erection clearly visible. She always looked, but didn't comment.

Every night, I would go to bed , with a raging hard on, I would smell her in the room, too afraid to even move. One of those nights, we weren't still asleep, each in our own bed, and I was so horny, that I thought I will get an aneurism, so I got up, and told her I am going to the living room, and if she would be ok not to come out until I am back. With a sleepy voice, she asked me "gonna watch porn", and we both laughed when I said yes.

So I did this two or three times a week, and always told her to stay away, and she would always have a comment, something like "you did it yestraday", or "again?", but every time it was in a joking fashion, so I figured she didn't mind.

Few weeks later, during one of those nights, she suddenly got out of the bedroom, saying loudly "don't mind me, I got thirsty".

The sound of her voice, and the sight of her, made me cum instantly, and I just covered myself with a blanket, until she got back in the room.

These late night visits weren't frequent, but after a while, she continued to do it. "Bathroom, passing through", or "sorry", and I just started edging, while waiting for her to come. I stopped covering myself when she would pass by, and with corner of my eye, I was looking if she was looking my way. She was.

As soon as she would be back in the room, I would cum. So, I wanted a next step, to cum in front of her. I edged for seven days, yes, seven days, without cumming, during the day, while at work, my balls were hurting, and I just wanted to give her a show. It wasn't intentional, I must admit, on day three, I had my living room session, but she didn't come out, same on the day five, but on the seventh day, I almost lost all hope, when I heard the door open. At this point, she didn't even speak to let me know she is coming through, she just went to the bathroom.

Now, the couch was facing slightly towards the bathroom, with a bedroom door being behind. As I saw her coming out, I started blasting. I didn't look at her, I just saw her shadow standing there, it was so hard not to moan, since I shot three giant ropes of cum all over my chest.

"Jesus fucking Christ, man, we must find you a woman."

I felt a great deal of shame, at that moment, and this perfectly describes our relationship. It was obvious that she didn't want me, and there was some sourness in those words.

Yet, this continued, and one night, when passing by, she told me "this is stupid, if you have to do it, do it in the room, it is the same for me at this point, I saw your pecker a thousand times".

So, I did. She would just sleep, but with a few little changes. She stopped wearing pj's, because "this spring is too hot", even though we've been living together long enough, that I know that she wore her short summer pj's last year. I knew when she was sleeping, and when she was awake. While sleeping, she would cover herself totally, I guess she felt cold, like most women tend to, but when she was awake, she would "accidentally", uncover her bottom, for me to admire it.

One night, while I was doing it, she turned my way, looking at me. "What are you watching?"

"You don't wanna know"

"Ah, cmon..."

"Two guys one girl, a threesome."

"What are they doing?"

"Double penetration"

"Ewww, that sounds gross"

And she just turned around.

It was all like this, I can't even remember all the instances something similar happened. The funny part is, besides this, we still clicked perfectly, hung out every night, joked around, but it was obvious that she wasn't into me.

One night, we were drinking up to late at night, and I wasn't planning on wanking, since I was almost wasted, as was she. When we got to our beds, I almost fell asleep, when I heard some movement. Turned around, she was on her stomach, with her bottom uncovered, wearing a silk tongue (who wears that to sleep), and she was touching herself, with her hand, which was underneath her, while reaching between her legs.

"What are you doing?"

"Shut up, you do it every other night, I can do it once, can I "

I got up, and just couldn't ignore it. She heard me, she felt me standing over her, but continued. My hand reached between her legs, and I started kissing her ass cheeks, her legs. She pulled her hand back, and responded kindly,with moaning. I wanted to turn her around, but she made it clear that she likes it that way, tried to lick her pussy, from behind, but she kept her pelvis on the mat, but when my tongue reached between her cheeks, she perked her ass up, and let me have it. In under a minute of ass licking, she was done, moaning loudly, almost screaming.

As the thought of me mounting her was passing through my mind, she said "don't even think about it", and covered herself.

You can imagine how pissed I was. Still, this continued for a few more months, until one night, while we were hanging out, and drinking, she, while being quite tipsy, opened up, and told me that this whole thing became weird, that she loves me as a friend, but she feels this is sick, and that it has to stop.

I felt ashamed, and just sat there, like an idiot.

"I understand you, but, you know... Maybe I can suck you off, sometimes, I don't know"

I just got up, and unbuttoned my pants, and she did it, right there.

And, it became a thing. I was very careful not to overdo it, I would only bring it up when we had a fun night, when she had a few drinks, and felt good all around. I tried touching her, giving my best to get a reaction, but most times she would just move my hand. It wasn't frequent, maybe twice a month, and sometimes, she would do it mechanically, with no vigor, but other times, I could feel she was horny, since she flirted with my cock, looked me in the eyes, etc. One time, she even licked my ass. Not really, but it is the closest I ever got to a rim job, I was laid back on the couch, she was on her knees between my legs, going down on my balls, and as I wanked, while she was licking them, I lifted my legs a bit too high, to give her access to my scrotum, and she just went down, and went from bottom all the way to the balls, with her full tongue, crossing over my asshole. Not only did it make me cum instantly, she found it hilarious, and laughed like crazy.

This went on for another year, and I couldn't help but to fantasize, about her finally giving in, loving me, making love to me, since I couldn't imagine living without her.

Until one afternoon, she told me she is having someone over, and that I should relocate to the couch. She met him the day before. I could hear them fucking, she was moaning loudly, and the bed was fighting for it's life.

That was it, I had to move out.

It was fun, it was amazing, that period was the most interesting and intense part of my sex life, but you can understand why I feel bitter sweet, when thinking about it.

After I moved out, I have never seen her again. We were friends on fb, until she deleted her profile, and that was it.

One might think, that I felt the old urge, and passion, while writing all of this, but no, I felt miserable.

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Anonymous
@confessions
29 Nov 2024 2:36AM
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I have been lusting over this woman, I know from social events, for quite some time. She is my age, so early 40's, and we met in the theatre. I am a theatre nut, and visit one at least once a week, and during this one intermission, some three years ago, we kind of started chatting, about the opera we were seeing.

Next time we met before the play, exchanged a few words, and on the next intermission, a couple of weeks later, I saw her going through the crowd, looking for someone.

She was looking for me. That night we went for drinks, and it was a pleasant conversation. I must admit, I looked at her that way. She is a beautiful, slim brunette, little back heavy, which I like, a lawyer whose career leaves no room for anything besides this little pleasure. I work in film production, so my knowledge on the matter, regarding acting, and music, made her want more from me.

We started having sex in April last year, first with protection, now without. She tells me she is on the pill, but I still pull out, which annoys her, but besides that, everything is just fine. Anyhow, she doesn't have almost any time besides her work, so for us, it is just theatre, drinks afterwards, and sex at her place, once or twice a week.

Now, you will think, that there is not much to confess here, but, there is. I am married, to another career woman, who also has no time for me, except on the weekends, so I am loving my wife, and this woman, at the same time, for 9 months now, without any problems.

Only thing I have to do is, to avoid weekend theatre.

Yet, I feel great amount of fear, since I am aware that this can't go on forever, without one of the noticing, and I must end my affair, but it is so hard to let go of something so great.

I only hope I will manage, before I cock it up.

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Anonymous
@confessions
01 Oct 2024 2:20AM
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I fucked my wife's friend.

She is, actually my SIL's friend, but my wife knows her, as well. She is a very beautiful brunette, I think she is 39, slim, with big tits, and all in all great figure. I am married for a long time, and my wife and her sister are very close, so I heard a few things about her friend - she was unhappy in marriage, cheating frequently, and all this was said in the tone of "she is acting like a slut".

And she was always super flirty with everyone, even me, but I guessed that is just how she is, never gave any extra thought to it, until she started going to my gym.

Talked to her a few times, she was giggly, flirty, like always. I must admit, I did position myself to get as much eye candy while she worked out, what can one do, I am a man after all. Soon enough she started asking me for advice, on how to do certain exercises, and I gladly helped, and, we started working out together, where we would even text back and forth, and schedule our next sessions.

I told this to my wife, didn't want her to find out any other way, and she didn't mind. Well, that was a mistake.

This woman wanted me, and she didn't hesitate to make that clear to me. I was in doubt, with a clear head, I would never do it, but our sexual desires are hard to control, especially when we have someone just offering themselves to us.

So, one evening, after our work out, I asked her to come over for coffee. She asked if my wife is busy, will we be bothering her, and when I responded that her and the kids are away for the weekend, she said yes.

We both knew what was gonna happen, and as soon as we got in, started kissing. I couldn't hold myself, I bent her over on the sofa, and pulled her leggings down. I wanted to eat her sweat soaked pussy and ass, but when I ran my hand over her lips, she was wet as a fountain. So, no time for that, and I just stuck my cock in her.

I fucked her hard, fast, with full thrusts in and out, while slapping her ass. Oh, how hard she moaned. In the end, I pulled out, and came all over her ass, making sure to cover both of her cheeks. She smiled, pulled her leggings up, without even wiping, kissed me, and said she has to go, her husband is waiting for her.

At that point, I didn't care what will happen. I figured, this is a start of something, that I will fuck her many times, even started going through scenarios of what I might do next, got hard again, and even jerked off, the same night.

Well, tomorrow morning, she texted me that she is changing gyms, and that she wanted to thank me for all the help I gave her in her work out routine.

I think she got cold feet, being afraid that if this comes out, she will lose all of her friends, and that is true.

And I am left here, thinking of all the things I could do to her, that night, that I missed out on. Still, can't complain, had sex with a hot woman, what more can one ask.

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@confessions
16 Aug 2024 4:17AM
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Now this wont be too exciting to some, but this one is mine.

First time confessing. I am married for 17 years, 41 now. Grew up in a small mountain town, which is a popular holiday spot, mostly for skiing, but since summers have became so hot, many people try to find refuge there, during the summer.

Since I moved out to the city at the age of 18, eventually, I got married, and bought myself a nice condo there, for ski trips and summer get aways.

Now, last two weeks I was there with the wife, and on the first weekend, her sister swung by for a weekend get away, since her husband and kids were somewhere on the coast, and she had to stay in the city and work. And, no, this is not related to either of them, directly.

We went out to this super popular club, that usually host people over thirty, and it was fun, we danced, got drunk, and made a show out of ourselves. Now I must mention, that a lots of locals visit this place, and my wife and sis in law, are kind of a spectacle (both hot, and both blondes), and since many people there knew me, we were getting many looks, cheers, a few rounds of drinks, etc.

One of the onlookers, I spotted, that couldnt take her eyes off of us, was this girl I knew when I was still living there. She was a hot brunette, now blonde, that I tried to do something with, but she had an older bf, who she, as I later found out, got married to.

She waved at me, I waved back, but she didnt come over to say hi.

After the weekend, wife decided to go back to the city with her sis, and I decided to stay till last Monday, since I had few more days of vacation.

So, last Saturday, I went back there, knowing I will find someone to talk to, got a place at the bar, and soon enough, few people came by, we were talking etc, and eventually, she entered. Short, tight dress, not so usual for a woman in her 40s, but she still looks good, very, very good.

She came to me right away, kissed me on the cheek, I got her a drink, and we started talking. It was obvious she wanted something, I just didnt know what. We went on a trip down memory lane, she got married soon after hs, her sons are 19 and 17 years old, and she has to go out with her friends, since her husband acts like an old man. I asked her, where are her friends - she told me that that night, she went out alone.

I started my confession about my marriage etc, and she stopped me - she saw us last weekend. Who is the other woman? My wifes sister? Oh, they both are so good looking, they dress so well, everyone talked about you the last time, etc.

I sensed a moment, so I told her that she looks as good as they do, maybe even better. The smile on her face, shy touch on my shoulder... She was looking around if anyone saw her...

She wanted something, and I was slowly starting to realize, that flirt is certainly one of the things she wants.

So; I gave her my best spiel. I swear to God, as night went on, and drinks kept coming, she even started squirming from excitement.

Eventually, the music "became too loud", what an excuse ,ha, so I asked her if she wants to come over to my condo, I have some wine, we can talk in peace.

I saw that she was reluctant, maybe the flirting was all she wanted, but I shot my shot, and she just nodded her head, but asked for me to wait for her outside, since she has to go to the ladies room. She didnt want to be seen leaving together with me...

I opened up a bottle of wine, after an hour one more, and our conversation leaned back against our love life, back then, and now. I was trying to play hard to get, telling her that I was always mesmerized by her, and that, last weekend, when I saw her, I wanted her to say hi, and that I was so happy that we managed to catch up that night. She confessed that she liked me back then, but that she knew that I will leave to pursue better things in life, and that her husband was a safer choice.

That is when i kissed her, and she kissed me back. Felt up her ass - damn, so round and firm. Maybe I reached under her dress too soon, and it seemed like that woke her up, so she just said no, and got up, wanting to leave.

"Please stop"I stopped her, turned her around, and went back to kissing. Again, she kissed me back, so I pressed against her, so she could feel my boner. She woke up again, and turned around to leave, and I grabbed her from behind, hugging her, pressing my cock against her round but - she pressed back, and I told her that she mustnt leave, that I never cheated on my wife (that was a lie), but when I saw her, again, last weekend, that I couldnt stop thinking about her, and that even, when I got back home, made love with my wife, thinking of her.

She turned back, and kissed me, told me she cant cheat on her husband, that she wants to, that her body wants me, but she just cant.

I shot my last shot, even thought it was risky - at least give me a blow job then, that really isnt cheating.

She was thinking about it, and before she had the time to think it through, I lead her hand to my crotch, and she started unbuttoning me.

I dont think I have ever seen a woman, that hungry for cock. She took it all in, and almost immediately, put her hand between her legs. She was selfconscious about it, so I tried to help her:

"Oh, I want you so much."

"Oh, you are so beautiful"

"Oh, I want to fuck you right now."

"Damn, you are fuckable, you are perfect, I wanna bend you over that table."

I hoped it will get me inside her pussy, and these worked, but in a way that she started rubbing herself underneath the dress, while swallowing my cock all the way in.

I felt when she was about to cum - she forgot about her head game, became sloppy, focused on herself, so I pulled my cock out, started wanking, and told her I am close too.

I wanted to wait for her to start cumming, to see her squirm, but she was too beautiful, and moaning loudly, that I started spraying her face. The fact that my cum set her off (I like to beleive so, even though it just may be the good timing), is the single most hottest thing I ever lived through.

She rushed to the bathroom. I could see she was super ashamed of herself. I wanted to talk to her, but as she got out, she just mumbled that she has to go, and got out.

This happened last Saturday, since then, I have been jerking off to the memory of this night twice a day, and that eventually, lead me to share it here.

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@chicks
30 Jul 2024 9:41PM
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Beautiful Brunette yummy hot

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@confessions
13 Jul 2024 3:19AM
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I am 43, divorced, and about a year ago I started dating this pretty hot career woman. She is blonde, three years younger than me, never got married, making partner at her firm was her prime goal in life, and now, that she had finally done it, she wants to "settle down".

I was a bit reluctant, told her I am out of a bad marriage, that I need time, to get to know her, and cooled off all the marriage talk she gave me from the start.

It would be a red flag instantly, and I would get the hell out of there sooner, if the sex wasnt that good. I have had my fair share of experience, nothing special, have done a few things in bed, with a few women, but this one... Never been with a woman who fucks like a porn star.

Well, soon enough, I found out why.

She started talking about it from a far, you know, marriage talk was replaced by kinks, fantasies, etc, and we tried some of the stuff, like public sex, risky things, and eventually, she told me she used to swing, and that it might be interesting.

Who did she swing with, how this came to be, those were the questions I asked, and she gave me vague answers.

At this point "settling down" with her was out of the window, but curiosity got the better of me (and amazing sex), and I went down the rabbit hole of swinging.

I went to three parties - she was a celebrity there, everyone knew her. Even I got some "special treatment". First time we went, she immediately got one of her friends, a pretty good looking brunette, to "make me relax", and she lead me to a room, in which she gave me head. Great head.

When I got out looking for her, I found her in one of the rooms, on her back, with a man between her legs. I didnt stay to watch, got back to the kitchen and had a few drinks. She got back ten minutes later, and we stayed there for the rest of the night.

Sex got even better, to the point in which, I thought I was dreaming this whole thing.

Second time, we ended up in a room with a couple, about ten years older than us. She was a fragile, tiny blonde, cute face, but still looking old. My girl was sucking his cock, and I noticed, that it was the smallest erect cock I have ever seen, and the though of me power fucking the wife of a sausage man, made me go balistic, so I pounded her like there is no tomorrow. Husband quickly came on my girls tits, and then they both laid next to us, and watched. With a condom, I can go all day, so this lasted for a while, and it was hot.

For the third time, we started drinking heavily at the very beginning, and after a while I was like, fuck it, I am just gonna hang out tonight. She got lost at some point, since we both felt quite comfortable now, and I decided to look for her.

Found her in a room with a man she was with on the first night, decided to stick around. He was taking her from behind, and she was pretty vocal. Something looked off, so I came little closer, and saw that he was in her ass. She turned her head towards me, at some point, as I stood there like a lamp post, smiled at me with the most beautiful smile in the world, and as he proceeded to go harder, maybe even aroused by this non verbal interaction, she started screaming, while looking at me.

Later that night, when we got to my place, I fucked her for three hours, and it was the best night of my life.

After that, I broke it off.

That smile made me realize, that I love her, and I can not be a cuck.

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@confessions
23 Jun 2024 5:28PM
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ROUND TWO / DAY TWO:
This will be a long one!

As a follow-up to the story I posted a week or so ago, here's how things played out during Day Two of my visit to SW Minnesota and my long-time red-haired FWB, whom I will continue to refer to by her first initial: T.

It was Monday. We'd spent the previous evening – our first night together since 2021 – watching TV while she got high, which always makes her extra-horny, We ended up having sex into the wee hours (about three hours' worth of sucking, fucking and pussy-eating), despite the fact she'd declared at bedtime that she was uncomfortable with her weight gain due to her taking anti-depressant meds, and therefore didn't feel "sexy." But she had second thoughts after we’d been in bed in less than 15 minutes. She claimed not to have had sex in more than five months (which turned out to be not entirely true, as you'll read later), so the left side of the sexual equation Cannabis + Desire + Dick Proximity was clearly greater than (>) the right side, which was Continued Abstinence + Self-Image Discomfort.

T babysits her grandson every Monday through Friday afternoon, filling in the gap between the time her daughter leaves for a factory job at 2:00, and the son-in-law returns from his chef's gig at 5:00. This commitment was the reason we weren't spending the entire week in the Twin Cities, as I'd originally planned. We negotiated staying at her place for two nights, me driving on my own to St. Paul for Tuesday, Wednesday and Thursday nights, and then returning midday Friday to retrieve her and go back north for the weekend.

Given the late hour when we finally finished Sunday night, it was well after 10 a.m. by the time we climbed out of bed. I'd been rebuffed (gently but firmly) against a morning fuck, so instead we got dressed in separate rooms and she made us French toast for breakfast (at nearly lunchtime!) before hanging out at her place for most of the day. Since she'd quit her meds due to the weight gain (an increase from 115 pounds to around 140 on her 5'5" frame), I was concerned she was reverting somewhat to her agoraphobic ways -- not wanting to go anywhere -- but she insisted she was just tired ("And you clearly know why," she declared in a half-joking, half-accusatory tone). The other underlying factor was this: When I say there’s nothing to do in her town, I mean THERE’S NOTHING TO DO. Instead, we watched TV together for a while, I started a book (“The Collected Works of Franz Kafka”) I’d purchased the previous evening at the town’s lone bookstore, and we exchanged stories about the events we'd each experienced since we were last together, which was October 2021. T had quit her retail management job at the peak of COVID, another in a long line of employment bailouts on her part. “I always end up the victim of two situations,” she said, by way of explaining her less-than-stellar work history. “Guys are always hitting on me, which I hate, and my female coworkers resent it and stab me in the back.” I suggested that’s what happens when you live in a small town, with its limited gene pool and where everybody knows your business. “I’ve been here for 30 years, and it never gets any better,” she lamented.

Meanwhile, at the end of 2021 my partners and I had sold our consulting business to our largest client, the related management contract we held for a micro-brewery in Croatia was taken over by Zagreb’s largest brewery, and my partners retired while I stayed on to continue my tech-writing work. I tried to pry some sexy stories out of T’s memory hole, but she said those needed to wait until evening. In our past meetups, we’d regularly used tales of prior escapades to help whet each other’s sexual appetites (and WET certain other things!), such as the time I hosted a young hottie along with my former gang bang buddy, and experienced my first (and so far, only) DV. Or the time T finger-banged a young woman after spending the day at the Minnesota Renaissance festival. They went at it in full view of the golf-cart guy who’d driven them to the remote parking lot. T admitted to me it was possible her paramour wasn’t exactly “of age,” but acknowledged it was the young lady’s first girl-on-girl experience.

By this point in the afternoon, it was time for T to retrieve her grandson. He’s a rambunctious two-year-old who is already showing signs of ADD, but after she brought him back to her place, I managed to get him to sit still long enough to read him a story. Apparently, that was a major milestone, and I received kudos from the dad when he came to pick up the short person a few hours later. At 4:00, T had a Zoom call with her therapist, so I took a drive in order to give her some privacy, returning about 90 minutes later.

“Do you want to know what we talked about,” T teased upon my return. “Isn’t there such a thing as doctor/patient confidentiality? I asked. She replied, “It’s OK if the patient divulges the info, doofus.” I love it when she calls me endearing names! I acquiesced and prepared myself for a fairly boring storyline, but it turned out rather fascinating.

“We spent most of my 50-minute session talking about you, actually” was her opening salvo. I responded with, “Well, that sounds totally boring. You should probably ask for your money back.” She reminded me her therapy sessions were free, based on her minimalist income and the charity of the county government. “You still got robbed,” I said, only slightly tongue-in-cheek. Here’s the gist of what she told me (edited for brevity and my semi-faulty memory):

“I told her in our last session that you were coming to visit, so we started out talking about how you and I had met all those years ago, when was the last time we’d gotten together, and if I was *ready* to have someone stay the night. We’d previously talked about my lack of sex since the year started, and whether I felt ready for the two of us to fuck. I told her we had a great relationship, always enjoyed each other’s company in and out of bed, and that you’d back off if I wasn’t comfortable – which you did. Then I told her I’d been too high to miss out, so we had this amazing session that lasted three hours. She wanted to know if I was planning to go for another round, and I said I hoped so.” That elicited quite the eyebrow-raise from me, but I refrained from making a snarky comment, so she continued.

“She wanted to know how serious you and I were, and I explained how there’s no way we’d ever live in the same city, but I felt better about having you around. I also told her you’d offered to take me to France in 2022, but I was too freaked out to consider going [Ed. note: I ended up taking my friend Liz, a 38-y/o Denver woman I’d met on a dating site, with whom I’ve been having occasional sex], but that you suggested I could come with you to Italy next spring, if I felt up to it.”

The previous day, I chastised T for not applying for her passport, for which I’d prepared the paperwork and given her the $175 document fee, while also floating the idea of her coming with me to visit Milan and Florence. “I’ve always wanted to see Florence,” was her dreamy response to my suggestion, but I’m not holding my breath on that one.

Anyway, as we were about to continue the discussion, her son-in-law showed up to collect his rug-rat, who’d been doing who-knows-what in the rear bedroom. I subsequently suggested we go somewhere for dinner, but T offered to scour her pantry and cook something for us. We dined on homemade chicken tenders, rice, and a salad. Afterwards, she suggested we go for an early evening hike in the local state park, so we doused ourselves with mosquito repellent – it WAS Minnesota, after all – and trekked about three miles up hill and down dale, through forests primeval and meadows replete with wildflowers, before finally ending up back at my car. “Let’s go for a drink,” she suggested, so we drove a mile or so to the local country club and headed into the clubhouse. T ordered an incredibly complex Long Island iced tea, substituting one ingredient for another, explaining exactly how she wanted each element added and mixed, and what style of glass to serve it in. As for me, I ordered a hard seltzer and drank it straight from the can!

“You realize,” I said to her, “the only reason the bartender put up with your micro-managing antics is because you’re gorgeous, and beautiful women always get what they want.” Before she could respond, a young woman sitting a few stools away at the bar – herself a particularly tasty tall, svelte and very desirable brunette who couldn’t have been much older than 21 – slid over to sit next to us and declared, “He’s right, you know.” T asked, “Right about what?” “One, you ARE gorgeous, and two, I get the same treatment.” Previously, in situations like these, an in-depth discussion would have ensued, followed by T trying (and usually succeeding) to pick up the younger woman, or at least have them agree to meet later. I’ve been on the receiving end of a few MFF threesomes thanks to T’s ability to pull a variety of hotties, which has included waitresses, bartenders, and even a bridesmaid at a bachelorette party being held in a strip club. More than once, I’ve said to her, “Who knew the best possible wingman would turn out to be a red-haired MILF.”

But this time around, either her heart wasn’t in it, or else she didn’t feel that special “vibe” bi-sexual woman sense in detecting others of their ilk. T grabbed her elaborate Long Island concoction and beckoned me to follow her to a table out on the patio. After we finished our drinks, she suggested we stop at the liquor store and pick up some additional hootch. I’m definitely not a drinker – never developed a taste for it, plus it’s bad for my gout – but if T wanted to get a bit tipsier, who was I to argue? She decided on some god-awful Smirnoff Red-White-Blue cocktail in a bottle, and we went back to her place. It wasn’t late – only around 9:30 – but I said I wanted to take a shower and put on my PJs. She said she’d do the same, and when I returned to the couch to watch some TV, T was tucked into the far end and wearing only an extra-long t-shirt. “I couldn’t find my nightgown,” she explained, “so I just tossed on this thing.” She was sitting cross-legged on the couch, with her hand gripping the hem of the shirt in order to pull it down over her crotch. “Are you wearing anything under that?” I asked in as innocent a voice as I could manage. “I left on my sports bra,” she explained. “You know I don’t ever wear panties.”

Oh, how well I knew that! The last time we were together, we’d gone to a bar in downtown Minneapolis where a band was playing on their outdoor patio. She wore a filmy, knee-length dress and sandals, but nothing else. About halfway through the band’s second set, after she’d consumed a glass of Merlot and an Amaretto sour, she was sitting on my lap and I had two fingers up inside her pussy. The band was loud enough to mask her moans of pleasure, but any semi-observant person could have figured out what we were doing, if they’d cared to look.

In this case, by way of further explanation, T lifted up the bottom edge of her t-shirt and flashed me her pussy. The previous night, with the bedroom darkened to near-blackness, I’d only been able to imagine how things looked down there. However, under the bright lights of the living room, I was treated to a lovely view of her natural bush (neatly shaped into a red inverted triangle), a pair of engorged outer labia, and just a hint of moisture at the entrance to her vagina. I took this as some sort of invitation, but as I slid in next to her and started to run my hand up the inside of her thigh, she twisted away from me and tugged the t-shirt down again. “Let’s watch a movie, OK?” was her solution to forestall any action on my part.

Because she lives out in the boonies in a trailer park that’s not served by cable TV, she relies on some crappy five-dollar-per-month antenna subscription, plus about a thousand DVDs. OK, so maybe I’m exaggerating, but she has this gigantic zippered case filled with sleeve after sleeve of movie disks. They were arranged alphabetically by title (a nod to her OCD), but I didn’t have a clue where to start. “Any porn in there?” I asked innocently. She gave me that look – you know the one – that was a combination of scorn, disappointment and shock that I’d even assume such a thing. “My last boyfriend took them all when I kicked his ass out,” she said with a laugh. I asked her to make a recommendation, and rather than getting up to find the DVD herself – I was jonesing for a look at that lovely ass – she rattled off a title and instructed me to dig it out. I don’t remember what it was called, but it was some PG-13 fantasy film with a bunch of young actors I didn’t recognize, reciting lines that were less believable than a legal deposition by a perpetual liar, and special effects whose main claim to fame was NOISE!

Meanwhile, T was working her way through a second glass of that vile Smirnoff stuff, having also taken one of the THC gummies I’d brought with me from Colorado. Although cannabis was now legit in Minnesota, they didn’t have edibles on the list of legal substances, so she was happy when I showed up with a tin of pomegranate-flavored “happy candy.” She complained the gummies worked more slowly than the wax dabs she’d had the previous evening, but I was in no hurry. Besides, the vodka was apparently having some effect, since she kept moving closer to me as the movie slogged its way to its inevitable happy ending. I was looking for one of those myself, naturally!

“Are we gonna have another late night?” T asked, leaning hard against my side and pulling my arm up around her shoulders. “The sooner we start, the sooner we’ll finish,” I replied with a sly grin. She sat up and gave me a seriously passionate kiss. “The sooner YOU finish, you mean,” she said. Then she added, “Fuck, I’m horny!” followed by a giggle and then, “Wait – did I say that out loud?” “Say what out loud?” I shot back in an innocent tone. “Never mind, Zac. Let’s go to bed.”

I’d taken the precaution of popping a 5mg Cialis as soon as we got home from the liquor store, so I was seriously erect as I walked back to the bedroom. I’m not usually in need of pharmaceutical assistance, especially around T, but I had a feeling this was going to be a marathon event, so I wanted to be fully prepared. T had stopped off in the bathroom, so I stripped off my pajama bottoms and slid underneath the covers. She popped in a minute later, climbing over me to reach her side of the bed. As she joined me under the comforter and pulled me toward her, she felt my hard cock bump up against her thigh. “Well, I see you don’t need a hot story to get you in the mood,” she whispered into my ear. I reminded her she’d promised me one anyway, so she rolled onto her side with her back against me, and we spooned a while as she worked her way through a very interesting tale.

T’s EROTIC STORY: After some soul-searching and advice from a couple of girlfriends, she’d dumped 20-y/o “James the Boy Toy” on New Year’s Eve, primarily because he was boring, not very bright, and lacked ambition. Also, “I could put up with his premature ejaculations, because he has a big dick and got hard again fast. But he did a shitty job eating pussy, so that was the last straw.” T decided it was too much work to find some other guy, especially since the pickings in the area were slim, plus she was starting to freak out about her med-related weight gain. “My Rabbit became my best friend, although I tried not to use it too much, since I was worried about desensitizing my clit.” In mid-February, one of her former convenience-store coworkers had been invited over for dinner. During the evening, more than a foot of snow got dumped, and it kept coming down, which resulted in them being stuck in her double-wide trailer for three days. Thankfully they had plenty of food, about a thousand DVDs to watch, and a fair amount of weed. Donna was an athletic 5-10 Scandinavian blonde in her late 30s, slender with barely B-cup tits, and a firm butt. T said they’d never done anything remotely sexual during the six months they’d worked together, but the combination of isolation, cannabis, and having to share a bed got the best of them. “She saw my Rabbit on my bedside table and asked me how it worked. Instead of using it on myself, I pressed it against her panty-covered crotch and switched it on. Before you knew it, we’d stripped off all our clothes, the vibrator got tossed aside, and we were grinding against each other’s pussies like crazy. She had her first girl/girl orgasm, and things just escalated from there.” T admitted she talked Donna into going down on her, although, “She didn’t need much convincing, after I’d initiated things by munching on her cunt for nearly an hour.”

T probably would have continued her tale but, halfway through her narrative, I’d slipped my erect cock in between her thighs and she’d arched her back just enough so I could enter her well-lubricated pussy. It was easy to do, since both of us were naked below the waist. I held steady to keep from distracting her, but she suddenly stopped talking and started to thrust against me. I let her do most of the moving and waited to see how far she wanted to take things. “I’m too drunk to get on top,” she admitted, even though I hadn’t made any such suggestion. “Doggie me, OK?” It was more an order than a request, but I was happy to oblige.

At my age, my knees aren’t what they used to be – arthritis, you know – so I find it much more comfortable to modify that position. I withdrew from T’s pussy, climbed off the bed after tossing the covers aside, and grabbed her ankles to pull her toward the bottom edge of the mattress. She squealed a bit from the rough way I manipulated her, but after I spanked her ass and told her to get up onto her knees, she understood immediately what I was after. I clamped my hands onto her hips and hauled her as close to the edge as I could without having her fall to the floor, and then I thrust forward. Her wide-open pussy accepted my erection with ease, and I leaned forward with my knees pressing firmly against the top edge of the mattress for improved leverage. While standing up, I’m much more capable of fucking for a while, since rocking back and forth on my feet is far easier than doing it on my knees, where I find it necessary to use my arms to support my weight. T likes a long, hard fuck, where she can reach down and rub her clit with no worries about sudden withdrawal. The orgasms she experiences from finger-fucking and pussy eating are frequent and continuous, but the ones triggered via fucking can be incredibly intense and nearly exhausting for her.

Such was the case here, where I pounded her nonstop for a good 20 minutes. She was making a lot of noise, none of which came out as actual words but was more guttural. Suddenly she reached back to dig her fingers into my thighs, which indicated she wanted me to stop pumping, shimmied her ass against my crotch, and let out such a massive groan that I was glad the closest neighbor was two lot spaces away. It ended up being the most intense orgasm she experienced the entire time we were together, although I didn’t know that at the time. I wasn’t even sure how long she’d held her breath, but she finally exhaled loudly and flopped forward. I backed away from the bed, breathing hard myself, and admired T’s lovely thighs and dripping-wet pussy. Unlike the previous evening, she’d left the bedside lamp lit, clearly less self-conscious about her appearance. Either that, or she’d been too well-lubricated with alcohol to notice the room wasn’t dark. Either way, I was definitely enjoying the view.

T asked me for a glass of water. When I returned, I found she’d stripped off her t-shirt and sports bra. “Is it fucking hot in here, or what?” she asked rhetorically, using her right hand to reach for the glass I’d brought while simultaneously patting the empty spot on the bed next to her with her left hand. I slid in alongside after quickly stripping off my pajama top, pairing my naked body with hers. She set down the now-empty glass and reached across to run her slender hand across my chest and tweak my nipples. My cock had sagged a little during my trip to the kitchen, but her touch revived things down below. “You didn’t come yet, did you?” T asked while already knowing the answer. I explained I’d been too busy concentrating on staying hard enough to make sure she got off, which she had – massively. “OK, it’s your turn,” she declared. Roll over onto your back. I want you to pump that man-jizz down my throat!” Rather than setting up alongside me, with her body resting against my chest as she had the previous night, T climbed over my outstretched right leg and knelt between my widespread thighs. She wrapped the first two fingers of her left hand firmly around the base of my cock, slid her right hand down against her crotch, and lowered her mouth until it engulfed the length of my penis that extended above her hand.

I’m not a large guy – 5-1/2” from base to circumcised tip – so she didn’t have much difficulty taking the entire exposed length of my cock between her lips. I hadn’t wiped my cock off after we’d fucked, so I knew she could taste her pussy juices on it. One of the things she told me years ago was allegedly the easiest way to determine if a woman was bisexual. “If she likes the taste of her own pussy on your cock or your fingers, she probably enjoys the taste of someone else’s pussy, too.” I’ve never experienced evidence to the contrary, so it must be true.

T can be quite enthusiastic when it involves cock-sucking. I was fairly sensitive, given how much I’d used my dick over the past 24 hours – a lot more than in the previous month, quite frankly. Several times I asked her to slow down and lessen the pressure she was using at the base of my cock. Finally, she slid her hand down around my balls and massaged them gently while deep-throating me and even gagging a bit. I started to pump my hips, so she stopped bobbing her head up and down and instead let me fuck her mouth at my own pace. While all this was transpiring, she was rubbing her clit with her free hand and groaning loudly – not nearly as much as before, but enough to signal she was close to a self-induced orgasm. A few grunts on her part, coupled with my faster pace of bucking my hips up and down, and I cut loose with three healthy pumps of cum down her throat. Even though all the signs had been there, my ejaculations may have caught her by surprise. Nonetheless, she remained in place until I was finished unloading, swallowing every drop like a champ. I was too wound up to notice if she’d induced her own orgasm while I was spurting, but at that point I didn’t really care.

“Damn, Zac – how does a guy your age come so much two nights in a row?” I had no answer for her, so I simply said, “Beats me,” shrugged my shoulders, and rolled onto my side. T laughed, which meant her words weren’t intended as an accusation, only an observation. She climbed off the bed, declaring she needed some more water to clear her throat, and walked out of the bedroom stark naked. When she returned a couple of minutes later, she slipped her t-shirt back on but left the bra on the floor. A quick kiss goodnight sealed the deal, and we ended the evening lying bare butt to bare butt as I quickly fell asleep.

Part III to follow.

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Anonymous
@confessions
12 Mar 2024 7:36AM
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Not much, but enough for me to brag.

I am 43, married, and I was flirting with one of my coworkers, for quite some time. You know, sexy jokes etc, and she was the one that started it. She is in her 30s, really slim, tiny brunette, not beautiful, but cute.

Last weekend, I was out with some friends, we got pretty wasted, and decided to continue our night in the club, and I havent been in one for over a decade. She was there, also tipsy, stated talking, flirting. I was drunk, so I let it slip - "cant wait to get home, hit the shower and think about you".

Sober, I would never have the guts to tell that to any woman. But it worked, she took me by the hand and lead me to the toilet, and I got my first ever club toilet bj. I came like a horse, and she swallowed.

Now, yesterday, at work, she was super cheeky, winking at me, joking.

I feel danger, not sure what to do next.

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@confessions
29 Feb 2024 3:36AM
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I have done a dangerous thing.

I am 43, married, and me and my husband had a rough year. Without going into details, there was this tragedy, that struck someone close to our kids, and we had lots going on to help them get over it. In the process, our mental health was really bad, and we started therapy etc.

After a few months, I felt better, kids are ok, but hubby has become numb, and seems that he has started slipping further into depression. Our best friends, a couple our age, with whom we used to socialize every weekend, were there for us. At first, we needed our time, but after more than six months, we met up, like we used to. My husband ruined the evening, by being really down. Ok, we will try it again.

Same thing. So, I started seeing them, mostly my girl friend, once a week, for coffee, and we would catch up, and it would be so good for me, our talks had a healing effect on me. I told her that, thanked her, and she told me she will always be there for me.

Then, she had to travel for a month, due to work, and I was left all alone. It is hard, when you are coming out of a mental trauma, and have no one to lean on. So I called her, talked to her on the phone. It helped. She eventually told me, if I have no one to talk to, that she will call her husband to call us for coffeee (they were always inviting both of us, only my husband wouldnt come).

So he did, and I went by myself.

I cant quite pinpoint the moment I felt attracted to him, but I always was in a way, but never really thought about it. He is tall, and that is important, because I am really tall for a woman. Still, much taller than me, but unlike my husband, who is tall, with a bit of excess of flesh, especially on his stomach, he is built like an athlete.

His wife, my friend, looks so much better than me, she is a blonde, I am a brunette, she is a petite, slim beauty, with feminine and elegant posture, I am tall (still slim, but too tall) woman, who always felt self conscious about my back side.

On our third coffee meet up, he said he cant go out, and asked me to come to their home. I was the one who made the first move.

I went in for a kiss, he backed off, but when I grabbed his groin, he surrendered.

It was the best sex of my life. I came three times, and he came in me, twice.

After our heads cooled off, we agreed that this shall never happen again, and I am sure it wont. I feel like a total scum, bet he does too, I have repented, but I just cant stop thinking about it.

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Hungbig1
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@confessions
21 Jan 2024 1:16AM
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I really love my sexy eldest sister Bianca. I mean she turns me on so much! Has long brunette hair, nice long legs, big tits and a beautiful face! Top it off with an amazing personality! Im going to mention that I have strong incest thoughts about her and constantly save and print her fb pics on A4 paper so U can masturbate too! When I'm wanking over her pics the dirty, fetishes that go through my head are so dirty and hot as I say her name as I'm wanking and imagine that I'm having sex with her without a condom before shouting out aloud "Bianca I'm cumming" then blowing my big load all over her pic only imagining it was me cumming inside her!

Now I really want to tell her how I feel about her want to know how would she react if I told her that I masturbate to her pics and fantasize about having sex with her and cumming inside her?? Do you think she will think this is hot or that her younger brother is just a dirty, incest pig?? I really want to impress her and make her feel the same way!;)

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Curiously18
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@confessions
06 Sep 2023 8:05AM
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Holy fuck. I met a girl younger then myself with my husband. Brunette and blonde eyes just like my husbands. I wanted to ask her so badly. Her bf showed up and ruined any openings. I saw how she looked at my husband... Seductive. Cute. Beautiful.
Nz

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