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39
Anonymous
@confessions
05 Sep 2012 6:48PM
• 33,194 views • 0 attachments
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Here is how I got to mess around with two of my friends during our senior year of college. Names have been changed to protect identities. I will also warn you - this will probably end up long.

SO I knew Ashley and Sara since our freshman year. They had been roommates since the first semester, and we all had History together. We had been the best of friends throughout college, although none of us had done anything sexual together. My parents lived not too far from college, and they decided to take a winter vacation to a tropical The house was empty, which meant a perfect studying place for exams. I invited Ashley and Sara to join, since I knew all of us liked studying together, even if it was for different classes.

I should take a moment to describe Ashley and Sara. They are really polar opposites of each other. Sara is tall and slender, white complexion, with (I would estimate) B cups, a flat ass, and blonde hair. Ashley is 6'2", a little chunkier, is a little darker (basically looks like she has a natural tan), has huge tits (they look like fucking watermelons), a huge ass, and brown hair.

We ate dinner at college first then drove to my parents house. We decided that it was a little late to start studying, so we decided to drink in my parents half finished basement (half finished as in my dad started to finish it, but got distracted and never completed the project). We had an old couch and a bean-bag like chair with a mini-fridge stocked with some of my dads beer. We broke out the beer and start drinking while talking about random topics. Ashley and Sara were on the couch and I was on the chair. Ashley and I were three beers in, Sara was still milking her second. This was on-pace for us, and based on past experiences, I knew we were all buzzed. I got up and went upstairs to pee. As I got to the top of the stairs, I heard Sara say that she was going to go pee too.

Now, my parents house has two bathrooms somewhat close to each other on the first floor. I figured I would be polite and went to the further bathroom, leaving the closer one for Sara. I partially close the bathroom door and pulled out my dick when I hear the door open and Sara say "OH MY GOD." I look over, and she is staring at my dick. I close the door in her face and finish peeing. After I finished, I opened the door and she was still standing there. She said "I AM SO SORRY. I thought you were in the other one, that door was closed. And holy shit you have a big dick."

Let me stop again and explain. I hate to brag, but I will anyway. Yes, girls are routinely impressed by my dick. That is because it is huge and long while soft, but does not get that much longer hard. It mostly just gets thicker.

Anyway, I didnt say anything and went back downstairs. Sara came running down a minute later saying "Oh my god Ash, you have to see his dick. It is huge." Ashley smiled and said that she has seen plenty of huge dicks. Sara said "Yeah I know. I mean, not to sound like a slut but I have seen a ton of dicks too, but it was really big even soft".

So they start talking about guys and their dicks for a while. I was starting to think they forgot about me when Ashley turned to me and said "well, now I am curious. You willing to show me?"

Ok, sorry for the interruption again. There really was no good time to mention this before. Sara and Ashley had both been single for a couple of months, and I had been single for about 5. I was pretty certain neither of them had gotten laid in that time span, since I would usually hear about it.

I laughed and said that I would feel a little uncomfortable just randomly taking it out, and that Sara only saw it because she accidently walked in on me peeing. Ashley said "So what, I have to wait until you have to pee again?" It sounded like she was waiting for an answer, so I said "yeah, I guess." She countered with "What if I showed you my boobs?"

Well that took me by surprise. And I think Sara was surprised by it too. I thought Ashley was talking out of her ass and would never flash, so I said "sure, why not." In one move she sat up and grabbed her shirt and lifted it up, showing her bra. Then she lifted her bra up and her boobs flopped out. Holy shit, they were big and perfect. I should point out that the couch and chair were only a few inches apart..we were sitting really close to each other. So they were almost in my face. She shook her shoulders and her tits swayed back and forth, then she pulled her bra back down, fixed her boobs, and pulled her shirt back down. Sara looked shocked (almost a little horrified).

Ashley looked at me and said "Ok, it's your turn." I really didnt want to, but I pulled my dick out of my pants. By this point, the conversation and staring at her tits had made my dick semi hard. I shook it a brief second, and Ashley said "that doesn't count, it is hard!"

I laughed and said "Well yeah, boobs will do that." Ashley said that she wanted to see it soft, so I told them to change the subject. So Ashley turned to Sara and started talking to her about some on-campus event later that week. All while I sat there on the chair with my dick out. And it only took a minute until it was soft. I saw Sara glancing at it out of the corner of her eye, and she turned and said "oh, it is probably soft again."

I looked down and confirmed that yes, it was soft. Ashley said "bullshit" and leaned over and grabbed my dick with her hand. I heard Sara yell "ASH, WHAT ARE YOU DOING??" and Ashley laughed and said "oh man, that is large and soft. Jeez, how big does it get?" She then started stroking it.

I kinda gripped the sides of the chair, not too sure what to do. It got hard almost instantly, and Ashley said "oh, not that much longer, but pretty thick." She didnt stop stroking though, and only a few strokes after she said "Uhm, I dont know where I am going with this..." and then she laughed. I said "yeah, what are you doing?" and Sara yelled "ASH STOP THAT!!"

From someone standing in the room, it was probably a funny scene: Sara staring (with a horrified and uncomfortable look on her face) at Ashley's hand stroking my dick, Ashley staring at her hand stroking my dick, and me looking at my dick, then at Ashley, then at Sara, and then back at my dick, all in a loop.

Ashley then looked at Sara and said "here, feel this." Sara yelled "NO! It's Mark...I wont touch his dick! And you shouldn't be either." Ashley said "Shut up, just touch it." They bickered back and forth for a minute before Ashley grabbed Sara's hand and forced it on my dick. Either Sara was not expecting it and didnt have a chance to fight back, or she just didn't fight back at all.

So Sara's hand was on my dick. She squeezed it and the look on her face went from horrified to amazement. "Wow, that IS thick..." She then picked it up and gently started stroking. She took both hands and gently stroked with both hands for a few seconds, before going back to one hand. Meanwhile, Ashley was still staring at my dick. She pushed her hair to the side, and then leaned over and put her mouth around the top of my dick.

Sara pulled her hand back and said "Ash, what are you doing now???" Ashley took my dick out of her mouth and said "Shh, I am just doing this for a few seconds." She then proceeded to take my dick back in her mouth and bobbed her head up and down my shaft. She actually got it pretty far down her throat. She held her finger to the side of my dick to show how far it went. She turned to Sara and said "Ha, beat that."

Sara said "I probably could, but we shouldnt and your mouth was just all over his dick." Ashley said "who cares..bet you cant do it anyway." Sara looked at my dick for a few seconds, then leaned in and put her mouth around the head and slowly it went down her throat. And it went further than Ashley...it didnt seem like it wasnt even that difficult to her.

She pulled up, then sucked a few seconds, bobbing up and down, then took it out of her mouth and turned to Ashley and said "see, told ya."

Sara and I then realized that Ashley's hand was down her pants, playing with her pussy. Sara yelled "ASH! Really? Right here in front of us??" Ashley said "oh shut up, its not like we have not masturbated before when sharing a room." Sara said "YEAH, but we were each in our own beds, with the lights off." Meanwhile, without thinking, I was slowly stroking my dick. Sara sees me and says "MARK! Come on, we aren't supposed to be doing this stuff together.." I shrugged and said "Ash started it."

Ashley stood up and started to take off her pants. Sara started to say something, but Ashley said "Come on, we are all good friends, let's each just have a little fun." She took off all her clothes and sat back on the couch naked, with her finger in her pussy. Ashley could see that Sara looked uncomfortable, so Ashley said "It's not like we haven't seen each other naked. You can just close your eyes if you want." Ashley then fixated her eyes on my dick and continued to stroke her pussy. I stared at her pussy and tits, and glanced over to Sara from time to time. Sara sat on the couch, looking around the room and , from time to time, at Ashley and back over to me.

I saw she was looking at my dick a little longer, and slowly started to reach her hand down her pants. Ashley saw too, and said "you know Sara, it isnt really fair that you are still clothed."

Sara thought for a minute, then stood up and slid off her pants, but stopped and said "this stays a secret..." then continued to take off her underwear, shirt, and bra.

I should take a break here and say that this all happened within a few minutes, but it really seemed like much longer.

Anyway, Ashley is slouched spread eagle on the couch while Sara's legs are conservatively spread. Both are looking at my dick, but Ashley is also glancing over at Sara. I think Ashley was getting bored, because she whispered "you have a condom?" Sara's hands stopped moving, and she just stared at Ashley. I said "yeah, probably in my bag," and I reached over and looked through the front pocket. I had a few, and pulled one out. Ashley got up, snatched it from my hand and ripped the packaging open. Before I could even move, Ashley had the condom on my dick and she was standing over me, rubbing my dick on her pussy lips.

Sara started to get up and said "I should probably leave you guys down here..." Ashley said "No, just stay. I dont care," and I just shrugged my shoulders. Ashley's tits were swinging in my face, and I grabbed her boobs and sucked on her nipples. I looked up, and she started making out with me. I could see Sara out of the corner of my eye, and she was looking at us and masturbating slowly.

She got up off me, and I thought the fucking was over. But she turned around and sat on my dick backwards, facing the couch. I reached around and grabbed her tits as they bounced. She grabbed Sara's leg and pulled her closer. Before Sara could say anything, Ashley was bent over and her tongue was between Sara's legs. Sara's eyes closed, her mouth opened, and for once she looked like she was enjoying herself.

Holy fuck, this seems much longer written out. My fingers legit hurt. I will come back later to finish. If you have reached this far, CONGRATS. I doubt many will actually make it this far though.

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6
Anonymous
@confessions
12 Oct 2025 4:01AM
• 378 views • 0 attachments
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I never thought that I will get to have a cuckold experience, as a bull, especially since I am neither young, nor endowed, but it happened.

She is my, lets say friend, I have known for over 20 years. I had a serious crush on her in our 20's, but she was too good for me back then, and that is fair, even now, she is way out of my league. But, in our 30's, we became FWB, but not on a regular basis, only when she would feel it, so, sometimes, 10 times in a month, and sometimes once or twice a year. I was her spare, I got that, but I didn't mind.

She got in a serious relationship some five years ago, and we kind of stopped seeing each other, in any capacity, and, well, it had to happen at some point, so I didn't give it much thought. But, maybe a month ago, she called me, to grab a cup of coffee, and well, I thought here we go again, but no, it was awkward, it seemed like she was with holding something from me, and when I asked her if she would come to my place, she said no, and rushed off. Two days later, the exact same coffee date...

I was puzzled, so I did something we agreed never to do, I started texting her. It took some time, a few days, and I guess it was easier for her to tell me over text, than eye to eye. She mentioned her fiance, is into cuckolding. I understood, immediately, what was up, so I was the one to encourage it, so the three of us met, at dinner.

He looked like he is about to faint, and he looked like someone who would love to see his woman fucked by another man - a total fucking wimp. She was talking, how they thought of it, how it would be easier with someone she feels comfortable with, etc. I was the one lightening the mood, joking, and she joined me, but when we parted ways, I thought, no way in hell this is happening, he looked like he regretted thinking of it. Two days later, she called, and set up a date night at their place.

The look, size and location of his place, answered all of my questions on why she is engaged to him.

I thought it would be awkward, but as soon as me and her started kissing, it was like he wasn't even there. They didn't ask for a condom, and I didn't bring one, hoping that we can do raw, and we did. He didn't jerk off, he just watched, fully dressed. It was amazing, better than it ever was, she came, loudly, and in the end, we did it in the pile driver position, and when I was about to cum, I pulled out, and did something I did many times before, with her, came all over her pussy, because, she has the fattest pussy lips I ever saw.

I was still tossing the last drops out of my cock, when he got up, almost ran up to us, I pulled back, thinking, he is about to hit me, but no, he got on his knees, and started licking my cum off of her pussy.

I am far from a moral idol, but that felt sick, so I got into the shower.

We are meeting again, next weekend, when he gets back from his work trip. I feel conflicted, but I guess that my cock will do my thinking, like it always did, and that I will continue this ordeal, even though, I felt pretty pathetic after that night, me, the guy who always thought sex is everything. I think I found my boundary, but I want to see if I can push through it.

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Anonymous
@confessions
14 Sep 2023 8:29AM
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I came on my girls face and felt terrible about it.

So here's a confession that will probably be comical to you, my girl and I think it is at least lol. So we were fucking, pretty intently actually and while I was fucking the shit out of her, I thought it would be hot to give her a facial because I had never done it before. While fucking her and getting close to cumming I asked her if I could cum on her face, she said yes and I was excited. So I started fucking harder untill I had to cum, when I had to cum I pulled out, ripped the condom off and assumed position above her face. I started jerking off getting ready to bust, I knew it was gonna be a huge one and I genuinely thought this was gonna be sexy as fuck. It finally got to the point of me cumming and I aimed, and I came......BUT as soon as the cum exited the tip, I felt so horrible, just thinking to myself "I am so sorry about this". Needless to say I completely COVERED her face with my cum, it got in her eyes and everything, the reason I felt terrible is because I have a great deal of love and respect for her, and to me I just disrespected her massively, it didn't help it started burning her eyes and she couldn't keep them open. We instantly started scrambling to find something to get it off her face and after we got her all cleaned up I apologized alot lol. She said it was fine she knew I wanted to try it but we both agreed not to do it again cause obviously she didn't like it either. Morale of the story for me, not everything you see in porn will translate to real life.

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12
Anonymous
@confessions
17 Dec 2014 5:05PM
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I am a member of the Loyal White Knights of the Ku Klux Klan and have been for a while now. I'm not going too say what state or what my ranking is because I will be beat & banished if they find out.

This 23 year old black woman (I'm in my 30's) heard about me being a member through neighborhood gossip and my friends coming over in their pro-white shirts.

One day I came home from work and she said "excuse me mister?" I was thinking "oh boy, here we go." I said "what?" She said "I'm not scared of your ass ya fucking cracker!" I replied "Well good for you ya fucking nigger!" I expected for her to go get some of her bang banging spooks after I said that but she walked up too me and said, "I think that's so hot! Call me a nigger again!"

I was shocked! I said something like "You're a crazy fucking nigger and I suggest you leave NOW!!!!" She did.

A few days later she said "Hello cracker!" I said Hello nigger!" When I said that she grabbed her tits and shook them at me!!!!!

This when on for months. One night I get a knock at my door and it was her! She asked me if i was alone and if I could talk? I said I was alone but that I really didn't want too speak too her. She then said "That's okay then, we don't have too talk, just put on your klan robe and fuck me!" She turned around bent over and pointed at her ass and said "You know you want too hit that shit!!!!"

I looked around too see if anyone was looking and I said "Hurry up and come in. I don't want too be seen talking to a nigger!" She freaking laughed at me.

I said "sit down and don't move because I know how you niggers are, always stealing shit!" She laughed her fucking ass off! It was like whatever mean and hateful thing I was saying was making her more wet and excited! I told her I would be back.

I went into my bedroom and was putting my hood and robe on with my back to the bedroom door and I soon as I turned around you was at my door! I was like "Nigger! I told you not too move!" As soon as I said that, she dropped too her knees and said (in a old time black Southern accent) "I'm sorry massa! I'm sorry massa!" I couldn't help it but I started to bust out laughing!!!

She was like "Mother fucker! taking this serious! This is my fantasy!!!!!"

I had a g/f who passed away in a car wreak and we has hand cuffs and whips. I went to the closet door, got out a whip and said something along the lines of "Nigger, you have very been bad! I ripped off her shirt and she coward down and scooted away from me. I didn't know if she was really fearing me or it was a act but as soon as I heard "Massa!! please no massa!!! It was all her ok.

I ripped off her tight jeans along with her panties and begun to beat her on the ass with the whip. As soon as I seen her pussy juice up, I was instantly hard! I was like WTF am I doing!!!! lol I pulled out my cock through my robe and said "suck my cock nigger!!!!!" And wow, did she ever! It was one of the best BJ's I have ever had.

My hood has a 3 buttons on the face mask so I can still wear my hood minus the face mask. I took the mask off. She way like noooo!!! I said Nigger, I'm going too eat your pussy and be smelling your pussy during my cross lighting's!!! She just laughed, so did I!

I kept thinking too myself, "I hope this nigger don't have aids..." lol

Anyway, after that I ended up fucking her with a condom on of course. It was a wild night. This was more than a year ago. Every time she sees me she says fuck you cracker and I say fuck you nigger. It was only a 1 time thing though I jack off and think about that night often...

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9
Jayphil
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@random
01 Jan 2017 1:38PM
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My DP partner and I got invited to a house party last night for NYE with about 50 people there. We got there around 6 already buzzed and so was most of the party. Unfortunately we saw someone there we had DPd before with her new boyfriend. It was really awkward at first but she came over and introduced him to us. We shook his hand and she pulls me aside and asks us if we'll fuck her again while he watches. Uhhhh yeah sure I guess I respond. I give my buddy a heads up and she leads us to an unoccupied bedroom with a fouton. We're in the middle of DPing her and I feel a tap on my shoulder. It's her boyfriend and he's got another couple from the party that wants to join us. I see that the it's the couple that owns the house and they tell us that Brianna(the woman we're already fucking) told them about her experience and it's always been something that they wanted but didn't want to use Craigslist or a stranger. Mind you we DPd Brianna only for one night and I got her pregnant(didn't keep it) because I didn't wear a condom when I came(I took it off and the reason for the awkwardness). I told the couple that we will come inside her and they needed to be okay with that and they were. I pulled out of Brianna's ass to watch the wife undress and as soon as her panties hit the floor she's mounting my cock. She was so much tighter than Brianna and she knew how to work my cock without me doing anything. Her husband is just standing there stroking his cock and I motion him over to put it in her asshole. This guy had a giant cock and I could feel it slide inside her already cramped pelvis(she was easily only 5 feet tall and 100 pounds. She came in the first 10 strokes and holy shit did she gush everywhere. After about ten minutes of him just punishing her asshole she started working both of our cocks together and I tell her that I want her to sit on her husbands cock while I try to make him come while fucking her pussy. I know that he's on the verge of cumming so she fits his cock inside her ass and leans back to present her beautiful pussy to me. I immediately started to fuck her as hard and fast as I can and after about 2-3 minutes she has a quivering orgasm which makes him and me cum. I pulled out and before she can get off of her husband my partner is inside her. I sit down on the fouton to recover and I'm just watching all of the fucking going on. Brianna and her boyfriend started fucking next to me and she starts blowing me to get me hard again...it works.
I got behind her and started fucking her asshole which made her boyfriend cum. She's disappointed because she's almost there so she slides him out and I slide in. I remembered that I wasn't about to cum in this girls pussy again and risk her getting pregnant again but she felt so good that I didn't care and I fill her up. I hear my buddy cumming inside the wife and Brianna notes that it's 1130 so we go watch the ball drop. Brianna cleaned up before but Andrea(the wife) just pulls down her miniskirt, fixes her top and hair and heads out full of cum.
We watch the ball drop, enjoy the music and I'm watching Andrea look sexy as fuck. I call Ryan over and tell him I had a great time but I didn't get to try out her asshole like everyone else did. He tells me to go upstairs and he'll send her up. I tell him to send her over and she can lift her skirt up in the back. He smirks and goes to tell her. She comes over and she tells me that she doesn't like the idea but I assure her that if she looks like she's just dancing with me, my buddy and her husband no one will notice. She complies and I slide out through my zipper and into her asshole. The two other guys run blocker as she proceeds to work my cock until I pull her hips to leave a balls deep creampie. She started to slide her skirt down and my buddy is inside her for the next 15 minutes. The husband wants a turn but she says she's too soar so he fills up her pussy instead. Finally she's able to pull down her skirt and we can see our cum running down her legs as she makes her way to the bathroom. We say goodbye and tell them thanks and to tell their friends. Here's to hoping for new and exciting holes to fill up this year.
Anyone else have any other stories?

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Anonymous
@confessions
04 Feb 2012 3:06PM
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So I recently started dating a 22 year old nurse in Philly, and shes fucking amazing. She said I'm her third lover and isn't that experienced. She's not lying, because she was so fucking tight and only felt comfortable in the missionary style for her. She then asked me to use a condom because she doesnt trust the pull out method and doesnt want to get pregnant.

Well I bought some condoms, and yeah after 6 years of not need them with my wife at the time... it fucking sucked! I cant believe what a distraction those things cause.

Long story short, I ended up popping it in her and cummed deep inside her fertile pussy. No the spermicide probably did the job and I should be okay.

But the following night I was fucking her with a condom, took it off when I flipped her on belly and ass up and begun to fuck her without a condom.

I shot a huge load in her and she didnt even notice!

About a week and a half went by and I decided to run my finger over her cervix which was hard to find because it was high, soft and closed. I think I just knocked her up! SHe was complaining of pain in her uterus last night!

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CuckQuean_Cari
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@confessions
13 Oct 2012 9:20PM
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I confess i love watching bdsm porn til lte t night and then walking round walmart, dressed like a whore..short skirt and tank top (with now bra or pnties).. teasing the men on purpose..bending over pretending to shop while they stare at my ass and my tits. I love standing close to them and hearing them breathe faster..i kneeled on my knees one night in front of an old man..about late 60's. My tits were almost falling out as i leaned over to read the condom packages..I looked up and sw his cock out and near my face..I rn to my car , he followed and i locked the doors..i pulled myy tits out and pulled my nipples while he jcked off on my door.. tht was over a year ago and I still com thinking about the fear running to my car then cumming..

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Anonymous
@confessions
01 Mar 2023 12:34PM
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My wife's BFF knows our marriage is open, and yes her and my wife have played around with each other. We came up with an open relationship contract of things we can do and things we can't do. Nothing about fucking her BFF was in the contract at all - and when I got the chance, I took it (who the fuck wouldn't, look at her!). I did break one rule, fucking another woman without a condom. So I thought that the encounter was fun, but I got a few text messages from my wife and she was pissed the fuck completely off.
"Why would you fuck her, of all people?"
I explained I was horny, and that she's fucked her too so I thought it wasn't a big deal.
Turns out she has feelings for her, and she feels like I somehow betrayed our open marriage contract - not because I didn't use a condom, but because I fucked her BFF.
I get a text from her BFF about the pic I took, telling me to show it to my wife so she knows I didn't cum inside her (I guess her and my wife got into a big argument because my wife thinks I came in her BFF because - well I don't like pulling out at all, but out of respect for my wife I came on her BFF's face).
I called my wife at her work, and she was like "that's your thing, you never pull out and I know you came in her!"
So I told her I took a picture of me cumming on her BFF's face. She was silent but wanted to see it.
I sent it to her via text.
When I got home from work, my wife was home - we sat down and discussed everything, including her feelings for her BFF. She cried a bit because she felt betrayed, and hurt not just by me but her BFF. I told her that it could be a lot of fun if we incorporated her into our marriage and that maybe we wouldn't have to have an open marriage because we both like her BFF... She thought about that for a bit - but said that she is in love with both of us and it just would take some time getting used to, but that she would think about it because it's the "best option."
So I told her BFF to take her out on a date tonight, take her to a nice restaurant, take her to a hotel and fuck her good, and that I can't wait to get the sloppy seconds. Her BFF texted back, "perhaps you'll have two sexy ladies on the menu tonight..."
3some? Dick is hard just thinking about it. Maybe I'll just sit back and watch them fuck and stroke my cock until they invite me in... whatever happens I hope my wife chills out. It's a weird situation and I don't want to lose my wife over some bullshit.
Another text from her BFF, "Maybe she'll actually let you cum in me ;) - I know you'd like that."
I think that might set my wife over the edge, so I'll probably cum in my wife and have her BFF eat it out of her for starters.
Yeah, I'm posting this on ML - can't really post this shit on twitter or reddit lol - nowhere else and no one else to tell this shit to. Thing is, I think her BFF has wanted me for a long time, and I've kinda wanted to fuck her too - we've flirted, but never took it beyond that. Now that we did, I just hope everything pans out...

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