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First Time Anal Ends In Tears

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19
Anonymous
@confessions
14 Nov 2022 11:48PM
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I’m a 29 married mom and I’ve been fucking my boss. He’s 42 married and has kids. 

One night we went out with a few people from work. We have flirted a bit over time but this night was heavy on the flirting. It was a late night and as soon as the last person left his house, my boss turned to me and grabbed my ass. Grabbed me by the back of the neck and kissed me. Eventually we went to the living room and he made me suck his big cock. And it was definitely big. He wanted to go down on me and ate me till I came twice. Then he bent me over and started fucking me doggy. Hard. 

we did it all over the house. When he was ready he creampied me. About 15 mins later I figured I would go but he wanted more. He started fucking me again and eventually gave me a big facial. 
I went home at like 4 am with cream in me and on me. It was so hot. 

I thought that would be it. But we ended up sending sexy texts and pics back and forth. One day at work told me to wear a dress the next day so I did. I came in and shit the door. He flipped up my dress and started eating me. Eventually he bent me over his desk and creampied me again. I went back to work with it dripping down my leg. 

we did it one more time. He had a party and his wife passed out. After everyone left I stayed and sucked his dick in his kitchen. Then he wanted to put it in my ass and I let him. He came on my face again. Then told me he’d put it in his wife later that night. He sent me the proof. 

I can’t wait to fuck him again. 

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Anonymous
@confessions
11 Jan 2023 7:24PM
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So... Has anyone ever given/received a creampie surprise?

I'm not proud of this one, but here goes...

I met a girl online and drove to her house to hookup.  She was... Out of my league, to say the least, even though I feel pretty confident in myself.  Tall, skinny, brunette, and more confident than me.   When I was texting her that I arrived, she told me to go through the backyard gate and come around.  I felt a little weird about it, wondering if it was too good to be true, but I did so.

She was in the jacuzzi next to her swimming pool, and I was awkward meeting her for a moment, because I was never told to bring a bathing suit.   She just laughed and said "join me naked", and she turned a bit and stood up to wring her hair out, giving me a view of sideboob.  I did as she asked and started to get in with her... It was cold, and I was hoping she wasn't looking, because I'm definitely a grower-not-a-shower... She totally was, and didn't look disappointed, so either she picked up on that or didn't care.  

She suddenly got a little awkward too and cuddled into me, taking my hand and moving it to feel her tits.  I started kissing her neck and she reached down to start playing with my junk... I got hard for her right away.   She sort of got on top of me, her ass against my cock, and I played with her tits from behind... They were probably b cup, but that was totally ok with me.

Then she balanced herself and bent over for me.  I started getting on top of her, having to grab the edge because I slipped.  I think she was trying to initiate more foreplay, but I really, really wanted her.  I was fully aware that the condoms in my pants pocket outside the hot tub were neither in reach nor useful in the water.  I didn't care at the moment, I wanted to fuck her.  

It was hard getting inside... She was so, so tight and small down there that my thick tip wouldn't even go in.  After her help and some maneuvering, I was inside.   I started pounding into her from behind, and it felt really good... It was far from the best fit for my cock, but it was pussy and it was amazing.   I was just watching the way she arched her back and picking up the pace... Getting more and more into it.

We'd hardly gone at it for a minute when I felt myself getting close.  I was really inexperienced at the time, and it was embarrassing to not be able to keep up.  I slowed down considerably and squeezed her tits from behind, telling her she was so sexy... I was trying to bide my time and recover, but it wasn't working.  She was so fucking sexy that I was going to cum whether I liked it or not.  

I really wanted to cum inside her, but I knew it was potentially risky and I was so embarrassed.  To be fair, we had talked dirty over messages, and one thing I mentioned was filling her with my cum, but it was in passing with other dirty suggestions, and she didn't give it any reaction in particular.  Having this in mind, I ended up giving in.

I felt my orgasm build and I picked up the pace considerably.  I bit my tongue as I kept thrusting, determined not to give myself away, as I started cumming inside her even as I fucked her.  I can't describe how it felt, because deep down to my dirty inside, I wanted to knock her up just because she was beautiful, and I just kept going, never intending to tell her.

She truly did not seem to notice.  

I, however, needed a moment to recover and felt myself deflating as I was thrusting.  Luckily, I think I lasted longer after cumming than before, and I think I shoved it far enough inside that she didn't know.    I pretended to lose my balance off the edge and blamed that.  

After that, we moved to some lounge chairs put together and started making out for a bit. She was playing with me, and I was taking annoyingly long to get hard again, but I blamed the cold air.  Once I was ready, I got on top of her and started fucking her again.  This time, we went at it for a little while.  Halfway through, she told me she wanted to suck my cock and swallow my cum.  As she was stroking it, I asked "So... since I've at least been inside you, are you on the pill or something?". She laughed and told me she had an arm implant.  She sucked me to completion as I pleasured her and made her cum on my hand.   It wasn't awkward anymore, but once we were finished we agreed to do it again.   Neither of us ever ended up reaching out though for a bit, and once I did, she didn't live there anymore.  

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Jayphil
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@random
10 Aug 2016 6:36PM
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About five months ago my two best friends and I went out drinking in Tampa and we ended up taking home two sloppy drunk chicks from the bar. I was DD that night so I drove us all back to the house. Tim and John sat in the back with Emma who was a redhead with a nice full D cup but no ass. She had John's cock out before we even got to the car. Most likely because the dude is hung like a horse. She was blowing both of them in the back seat on the way to the house. Maria sat up front with me and gave me a hand job the whole way home. Maria is a Latina with C cup tits but made up for it with an amazing fat ass and a tight pussy. When we got to the bedroom two buddies start fucking Emma and Maria starts blowing me. Tim got Emma to let him fuck her in the ass while John came over to get blown by Maria. We switched up women and Emma is riding my cock and John see's his opportunity for a DP and she goes with it like it was nothing. John slides in her ass and if you've never DPd a woman you can feel the other cock fucking the other hole. After about 10 minutes of John punishing her ass I cum balls deep in her pussy. That's when I realized my fuck up. My rubber broke fucking Maria and before I could get another one Emma hopped on my cock. I acted like nothing happened and John switched spots with Tim and I got her off me. I laid the for about ten minutes before Maria came back over and sucked me hard again. This time I put a rubber on and Maria hopped on my cock while sucking off John. But as she was riding my cock facing away from me I started fingering her ass. I also really wanted to cum inside her pussy too so I pulled down on the condom until I felt it break. By the time I came again I was four fingers deep in her asshole. John went over to Emma who was passed out and came on her tits. Maria hopped off my cock and put Tims cock in her ass. I slid my condom up so it didn't look like it broke. I was surprised that after about 5 minutes my cock was fully hard again watching Maria getting fucked and seeing that her pussy still needed a cock I went for it. She didn't want to at first but after a few minutes of rubbing my cock on her pussy she didn't resist when I pushed my cock with the still broken condom in. Tim slyly slid his rubber off when his cock had slipped out and he came inside her ass. I gave her a balls deep creampie for a second time that night. After she laid there for a bit she got off Tims cock and slapped him in the face for cumming in her ass, not realizing it was my cum too. She wakes up Emma and they catch an Über ride home. Come to find out I find them both on Facebook and they're BOTH pregnant. They both had boyfriends and they took ultrasounds together stating how far along they were and how excited they were on a post but the dumb bitches don't have their profiles set to private so I didn't have to contact them to find out that they're probably pregnant because I left my seed inside them.

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Anonymous
@confessions
04 Apr 2023 12:22PM
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It was back in the days of CL, where horny guys like me could post ads and find a side chick with ease. I found it was easy to do if you worded things right. I’d always get a few nibbles from real women looking to fuck. My insatiable hunger to fuck was barely satisfied from my home life, and my marriage was deteriorating because my wife lost interest in sex (hormonal issues). Wife eventually got the medical attention she needed, but she’s the one who opened up the marriage so that I could “go have fun.”
I’d post multiple ads, honest with my intent, “Married man looking to creampie you.” Turns out there is a lot of women out there who absolutely love getting seeded. I’ve been with all kinds of women, black, latina, and white. Usually, if the woman was overweight, they had a lot of issues and were very self-conscious so it was very easy to get in their pants. Not that I was a chubby chaser, but it was pretty much a guaranteed lay if she was fat.
This story is about Linda. Linda was (and probably still is) a nurse. I posted on CL just to see what was out there and I caught Linda’s eye. She sent me a photo of her standing in front of a bathroom mirror, showing some cleavage. I responded back that she was very beautiful, and I thanked her for sending me the picture. We emailed back and forth, I sent her my picture and she thought I was attractive so we decided to meet at a public place just to see if we were a match.
I met her in a park the next day after work. She was a very hefty woman, probably well over 350lbs. Linda was wearing sunglasses, and a long dress, and she had red lipstick on. Even with all of that, she wasn’t pretty to me at all. She took off her glasses, and I understood why she had them on, she was trying to hide that her eyes were misaligned, she had lazy eye. My mind was fighting itself, pussy is pussy, but she was definitely someone I could easily pass up sexually.
“Let’s get a hotel tomorrow, ok?” She told me, and leaned in for a kiss. I froze for a second, and then decided to go for it. Now I don’t know if she was playing a game, but when my lips met hers, it was just a standard kiss, she didn’t even open her mouth for my tongue. My tongue pushed through her lips and her mouth opened and she seemed shocked, like she’s never French kissed. Her tongue wasn’t moving, she seemed like she absolutely didn’t know how to kiss. I pulled away.
“You ok?” I asked.
“Yeah, I’ve just never been kissed like that,” she said blushing. I had my doubts, and didn’t believe her.
“Your husband never French kissed you? You never had a boyfriend kiss you like that?”
“Not like that, no.”
We parted ways and she said she’d pay for the hotel room. The fucked up part is that she lived pretty close to my house, literally 4 blocks away in the same neighborhood. She said she responded to the ad because it was near her and it peeked her interest.
The next day I left work early and headed to the designated hotel, I texted her telling her I was there. She texted me back with the room number, and that she was nervous. I didn’t respond back, just headed to the room, knocked and she opened the door.
She was wearing a red teddy, of which I could see her tits through it, her girth prevented me from seeing her pussy. I had second thoughts, of which she might have picked up on. Linda clenched my arm and ushered me to the bed.
“You can fuck me anywhere you want,” she said trying to be erotic. We started kissing, I removed her teddy and started fingering her. She had a nice soft bald pussy. I went down on her, but had to push some of the layers of fat up as she spread her legs. She moaned my name as I licked her and then told me, “I want you in me!”
She bent over doggy style, spreading her legs. Her ass wasn’t really anything to speak of, a bit flat. I seen her asshole puckering up at me and thought of giving it a try, but slid my cock inside her pussy. It was nice and warm. I started thrusting in and out, letting the tip barely escape before jamming it roughly back in her. She was wet, so wet my balls were soaked in her fluids and it was dripping down my leg. I pulled out and circled her anus with the tip of my cock, and she backed into it. We didn’t have lube and she wasn’t relaxing her anal muscles, so it was a losing battle. I got rough, and pushed as hard as I could trying to get inside her ass, she clenched the bed sheets moaning. The tip popped inside, and I began pushing deeper in her shithole.
“Oh, go slow, slow…” she moaned, gripping the sheets of the bed.
I don’t know what got into me, but I started thrusting my cock balls deep into her ripe ass. My hard cock was pulsating as I increased speed, slamming into her ass cheeks, watching her fat move in waves to each of my thrusts.
“FUCK!” she screamed, “Hold on!” I pulled out and she ran to the washroom. What followed was hearing her taking a massive shit, gaseous noises and all. Even with the door closed and the bathroom fan on, the odor was unbearable. It was nauseating and atrocious, I was thinking of getting my clothes on and leaving, but my cock was doing the thinking for me.
“But you didn’t cum in her yet,” my cock said.
“Dude, have some god damned standards bro, she’s ugly,” I told my cock.
“Pussy is pussy, when she comes back out, cum in her and then we can go.” My cock throbbed.
“Asshole,” I told him, “Such an asshole.”
She came out of the washroom apologizing, “I’m so sorry, it’s been a while, next time I’ll make sure I’m prepared.”
Linda laid down on the bed, spreading her legs, “Your ad said something about a creampie? Momma needs her cream filling!”
My dick, “See?”
I mounted her, stuffing my cock inside her pussy and started pumping. I closed my eyes, but then decided to look down at my cock going in and out of her. Her arms pulled me down for a kiss, her hefty tits wobbling as my pelvis met hers. Honestly it took me a while to cum. I hammered at her cunt for a good 20 minutes and finally my seed burst into her. Her fat hands gripped my ass pulling me deeper, and I released all I could inside of her. I rolled off of her, and laid there for a bit, she cuddled into me, thanking me.
I got dressed and she started making plans for our next encounter. I met her about three more times and then broke it off. It wasn’t that she was fat, it’s that she just wasn’t my type at all. I’ve banged fat chicks that were totally hot as hell, but she was just not attractive to me at all.
She was disappointed, telling me that she thinks she’s in love with me, but I told her that I didn’t have the same feelings and just wanted to go my separate way.
I’ve fucked at least 5 different women from CL, fell in love with one – but those stories are for another time. I wrote this story just to get it off my chest and get it out of the way. I have to confess she was one of the worst fucks I’ve ever had.

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Anonymous
@random
22 Oct 2016 5:11AM
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I confess my GF is a major cock whore when she is drunk and I love it. Whenever she drinks too much she wants to pick up 2-3 other guys at the bar and bring them back home with us. It usually involves just blow jobs for the guys while I fuck her brains out and she loves getting her tits covered in stranger's cum while I blow my load inside her. It is one of her strict rules that I am only allowed to fuck her, but I've been secretly breaking that rule on her.

It started out around her 26th birthday.. We were both really into creampie porn. My favorite was gang bang creampies where the girl would take and hold tons of loads then ride the last cock letting it all out. Almost every time we fucked it ended with me busting inside her. She said she loved the feeling of how hard I would get right before exploding and loved the feeling of my cock pulsing inside her. I kept trying to persuade her to take more than just me but she would go back to her one rule..

I posted a classified ad on craigslist on the day of her birthday. That night we went out with a group of friends to hit the local bars. We served her drinks one after another to have a good time. Around midnight I went and checked my phone to see about 20 emails about my ad. I went through and selected a handful of guys to meet me back at our place. I left the bathroom and saw the alcohol catching up to her so we decided to leave. On the way home she was all over me asking to fuck and trying to get in my pants. I told her she would have to wait for that until we got home.

We pulled in our parking spot and she was practically passed out in the passenger seat. I noticed more cars than normal by our place so I knew no one was flaking. I helped her out and brought her upstairs to the bedroom where I undressed her, at this point she was completely out of it. I went downstairs and let these 5 white guys into our place and led them up to the bedroom. They went in the bedroom with me one by one and would see her completely exposed to fuck her. I made sure they all fucked her raw and came inside of her. All 5 came and all 5 went as she laid there with a pussy full of cum.

I went back in the room and nudged her telling her how horny I was and I wanted to fuck her. She was completely clueless of what happened. She woke up in a drunken stupor dripping cum out of her pussy. She asked me what it was and I just told her she was really turned on from earlier. She hopped on top of me and rode me until I came with all the other guys' cum running down my cock.

The next morning she came into the kitchen as I was making breakfast and came behind me whispering in my ear that she loved all the cock she took last night.

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Anonymous
@confessions
03 Nov 2016 12:37AM
• 1,799 views • 2 attachments
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I confess my GF is a major cock whore when she is drunk and I love it. Whenever she drinks too much she wants to pick up 2-3 other guys at the bar and bring them back home with us. It usually involves just blow jobs for the guys while I fuck her brains out and she loves getting her tits covered in stranger's cum while I blow my load inside her. It is one of her strict rules that I am only allowed to fuck her, but I've been secretly breaking that rule on her.

It started out around her 26th birthday.. We were both really into creampie porn. My favorite was gang bang creampies where the girl would take and hold tons of loads then ride the last cock letting it all out. Almost every time we fucked it ended with me busting inside her. She said she loved the feeling of how hard I would get right before exploding and loved the feeling of my cock pulsing inside her. I kept trying to persuade her to take more than just me but she would go back to her one rule..

I posted a classified ad on craigslist on the day of her birthday. That night we went out with a group of friends to hit the local bars. We served her drinks one after another to have a good time. Around midnight I went and checked my phone to see about 20 emails about my ad. I went through and selected a handful of guys to meet me back at our place. I left the bathroom and saw the alcohol catching up to her so we decided to leave. On the way home she was all over me asking to fuck and trying to get in my pants. I told her she would have to wait for that until we got home.

We pulled in our parking spot and she was practically passed out in the passenger seat. I noticed more cars than normal by our place so I knew no one was flaking. I helped her out and brought her upstairs to the bedroom where I undressed her, at this point she was completely out of it. I went downstairs and let these 5 white guys into our place and led them up to the bedroom. They went in the bedroom with me one by one and would see her completely exposed to fuck her. I made sure they all fucked her raw and came inside of her. All 5 came and all 5 went as she laid there with a pussy full of cum.

I went back in the room and nudged her telling her how horny I was and I wanted to fuck her. She was completely clueless of what happened. She woke up in a drunken stupor dripping cum out of her pussy. She asked me what it was and I just told her she was really turned on from earlier. She hopped on top of me and rode me until I came with all the other guys' cum running down my cock.

The next morning she came into the kitchen as I was making breakfast and came behind me whispering in my ear that she loved all the cock she took last night.

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Ceddie0
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@confessions
06 Dec 2011 12:48AM
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I confess that I licked my girlfriend's asshole and played it off like an accident.

Let me set the stage. I am 23 and my girlfriend is maybe 7 months younger than I am. We met as freshmen in college and are both going for our master's degree. We've been dating for almost four years. She's never done any anal sex or play before and is pretty against it. She's not very sexually adventurous, she lets me creampie her but no facials or mouth shots. She'll suck me until I come and finish me with her hand.

About a week or two ago we were fooling around on my couch after a date at my place. We were both drunk and I had smoked some pretty good cannabis. I slide down to her jeans, take them off and start to give her head. She kind of worries about if she's clean enough for me, which is not bad but sometimes makes her apprehensive about just spreading her legs and letting me dive in. This is also partly why she is against anal. I find that she gets more comfortable with oral when I say things like, "You taste so good" so I said that to her. She responds with, "Oh taste me." This really turned me on and I really started trying to make her come.

I think she could tell that I was really getting horny and that gets her off. She asked me if I wanted to switch positions. I said, "Yeah what do you want?". She flips over onto her upper back and sticks her ass up in the air with her whole body facing in my direction and legs bent forward, if you can imagine. I start going to town on her and from this angle I can easily lick her hole which she likes. But this angle also gives me a front and center view of her asshole. Now, I've been staring at this thing for four years and I was really turned on. Because of the way we were facing, my nose was pretty much in her ass crack. I started to move my head around with my tongue motions but I was really just rubbing my nose in her ass. I could feel some light, fine hair since she doesn't shave that far.

As I'm working my tongue around her hole I slowly creep more south, each time going a little bit more. She hasn't said anything yet so I keep going. My tongue makes it's way in-between her vagina and ass on a couple passes. I press my face in and basically start sucking on the area below her vagina, for my angle above her vagina. At this point I'm almost about to flip her over and butt fuck her so I give in and stuck my tongue way out and licked her asshole. It didn't really have any taste, but it had more texture than I was expecting. She finally says, "Woah, what are you doing?!?". I was so worked up all I could say was something like, "Sorry, it was an accident. I went too far." She got upset and after some reassuring, I convinced her that I wasn't grossed out but somewhat embarrassed and that she shouldn't worry.

She was kind of turned off by it but she knew that I was still horny. She ended up sucking my dick and when I told her I was about to cum she stops sucking and switched to her hand. It was taking me a while to start cumming but I was really close. She switches back to sucking maybe because she thinks my orgasm is fading. I knew I was going to cum in her mouth and that got me so turned on that the last 3 or 4 licks were absolutely amazing. I had been erect for a while and that makes my cumshot much larger and shoot further. I start squirting cum into her mouth and she kind of jumps a bit, but keeps sucking and licking just under my head. I could feel that I was shooting alot because my whole groin region convulsed with each squirt.

After I had finished cumming she gave one last lick and suck then looked right into my eyes and swallowed. If I hadn't just cum I would have right there. I'm not really sure why she did it that night, but she hasn't done it since, just the usual suck and hand finish. It probably had to do with her being drunk and we had been pretty worked up before so I suppose it is possible that she got horny again.

I want to try slowly introducing her to more sexually adventurous things, starting with anal and facials/cum in mouth. I was thinking about trying to work our way to washing her asshole in the shower. She likes to take showers together so I think it could work. I'd love to one day wash her in the shower then just go to town with my fingers tongue. I think that anal sex itself is out of the question, at least for the time being. I don't have the longest penis but it's kind of thick and her pussy is really tight so I don't see anal sex happening anytime soon.

I also want to set up a video camera in my room one night. The problem is I can't predict when we're going to do anything and I don't think my digital camcorder can record for 6-8 hours. I was thinking about getting a webcam and hiding it somewhere and plug it into a dedicated laptop for continuous recording. Has anyone else had success for that long of wait time? It would be interesting to show her off, can't do face though sorry.

Anyway I think that's about all that I have to say. I hope you enjoyed my confession.
Ceddie0

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Anonymous
@confessions
08 Feb 2024 1:12PM
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My neighbor moved in with her husband 2 years ago. Her husband is an over the road truck driver, so he’s gone 6 days out of the week mostly. Sometimes he’ll be home for the weekend but for the most part he’s gone a lot. When he’s home he drinks until he passes out in the backyard, or go out to a bar. They have no children, so she’s all alone when he’s gone.
When he would leave, she would ask me to help her with little things, and being a good neighbor, I would always help the little lady. I’m 52 and my wife decided to leave me a good 10 years ago, so instead of going through a shit ton of financial loss (again), and having my heart break (again) I just decided that I didn’t want any relationships and that I’d just play the field and fuck whoever came my way. My neighbor (we’ll call her Jessica) is 36, and always wanted to chat me up when she saw me outside. I’d always be nice and friendly, talking about the weather, and just general bullshit going on.
We grew into pretty good friends, if she seen me outside sometimes she’d call over to me to help her with something – usually some handyman issue that her husband never fixed. Things really took an interesting turn 6 months ago, she called me over to see why her stove wasn’t working and I immediately found that the gas was intentionally turned off to the stove.
She knew I knew, and she knew she was caught. Jessica was embarrassed, and sat down on a chair in the kitchen and started to cry.
“I’m just so fucking lonely. I’m sorry for bugging you.”
I consoled her, told her that I was her friend and that she could always talk to me.
She got up, and hugged me really tight, I could feel her pushing her tits against me and her hands gripping on to my shirt as she sobbed.
“I’m really fucking lonely…” she murmured. Our eyes met, we kissed, and we fucked.
As you can see from the picture, Jessica isn’t a bad looking woman. Her raven black hair, her lovely tits – she’s got a lot going on for her. Since we first fucked, when her husband is away, she’s always over at my house and even spends the night sometimes. She’s admitted she has deep feelings for me, and I have to say I do have feelings for her too. We’ve been fucking behind her hubbies back for a good 5 months now, and I’ve never used protection. Little lady has a bit of a fetish for creampies, she says her husband never touches her anymore and they’ve been married for 8 years. She awkwardly admitted that she can’t remember the last time he came inside her.
She’s been talking about filing for divorce, selling the house and getting an apartment – but I told her that she didn’t need to get an apartment because she’s basically living with me when her hubby is away. Hell, my bedroom has bras and panties laying around half the time because she leaves her clothes at my house half the time.
When I told her that she didn’t need an apartment, she lit up and was excited.
“I totally would love to be in your arms every fucking night,” she paused, and blushed.
“I’m so fucked,” she said as a tear rolled down her face.
I was confused, “what? What is wrong?”
“You don’t want to know, I just realized something.”
I shook my head, “what is it babe?” And then I panicked a bit, “are you pregnant?”
She laughed, “no… not at all. I just realized I’m in love with you and it’s not just any little crush, I’m madly in love with you and I don’t know what the fuck to do about all this shit, I need to get a divorce. I’ll go see a lawyer tomorrow.”
My heart stopped, fucking hell time stopped, but words came out of my mouth that I wasn’t even trying to say, “I love you too.”
I fucked her again, looking into her eyes as I came inside her.
Currently she has filed for divorce; her husband didn’t seem to mind and doesn’t even know I’m banging his wife. He’s talked to me a couple times over the fence of our properties.
“You’ve been a good neighbor bro, but the house is up for sale and I’m moving away. She can go do whatever. We really lost our connection a while ago, she got mad because she found used condoms that I forgot to throw away in my truck. I mean you’re a man right? When you’re on the road and some cracked out lot lizard is pounding on your door for a $20 fuck, why deny it.”
I just nodded my head, “yeah men have needs.”
He grunted, “yeah, the fuck she think happens on the road? She’s a dead fuck anyway, fuck we haven’t fucked in probably two years.”
That was the last time I saw him. Jessica is living in the house until it’s sold, but always comes over – she has a key to my house. Every night we’re having fun, she makes me feel like I’m 18 years old again. I’m not sure that we’ll get married or anything like that, but it sure is nice to have a beautiful woman in my arms every night. Jessica is planning on getting off her birth control pills, she did ask me if I wanted to be a father – and I told her that I’d love nothing more than to inseminate her beautiful body with my cum. So, I might be breeding her soon. Fucked up thing is, that’s her word for it, “breed me daddy.”
She likes to be on top and loves doggy style too. Gripping her soft tits while I cum inside her is fucking amazing.
She knows I go on porn sites, we’ve discussed it because I brought it up a while ago. Jessica actually loves watching porn, and doesn’t care that I take her picture. I hope Jessica stays with me for a while. She’s a very nice woman, literally tells me what’s on her mind, we talk about all kinds of shit, 100% open and honest with each other too.
Sometimes life sucks, but if you wait and let it flow, it will reward you.

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15 Dec 2016 7:42PM
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My loser exroommate who I am not friends with at all has no idea that I've been fucking his girlfriend for the past 4 years and he's paying for 2 kids that I fathered. She's way out of his league and I think the only reason that she is with him is because they lost their virginity together and they split the bills. He constantly neglects her and goes out with his friends without her. The first time I fucked her I came home from work around 9, showered and passed out on my bed naked because no one was home. I get woken up by her with my cock in her mouth. I yelled at her and she apologized and said she came into wrong room by accident because she was out drinking. I noticed that she's got her skirt hiked still playing with her pussy while she's apologizing and I know that she's seeing my cock get hard. She sarcastically asks me if I like see because I'm getting hard. I nodded and she asks me if I want her to suck me off. I grabbed her hips and pulled her onto the bed. I had only planned on letting her blow me but when she moved to put my cock in her pussy who am I to argue. I creampie her pussy two times and she gets a text message saying her boyfriend will be home in an hour. So she goes to shower and I think that's the end of it. Two days later he heads out with his friends and she's in my room taking my cum. This time I worked my cock into her asshole. After I cum in her she informs me that it's the first time a real cock has been in her asshole. About two months later I'm in my room with my cock planted firmly inside her asshole(standing up from behind against the wall) and him and his friends come into the front door. She started to freak but it turns me on more so I gag her with my tie and punish her hole as hard as I can until I hear two of them come down the hall. It's his dumbass and his best friend bitching about her and the fact that she makes him wear a condom all the time. By that time I'm back in pussy that causes me to lose it and fill up her. Fast forward 4 years and she's carrying child number 3 of mine. The only reason she hasn't left him for me is because I don't want that kind of a relationship and she's content with the situation. She still hasn't given up her asshole to him she keeps that just for me.

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@confessions
17 Nov 2020 4:45PM
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so last night i got very very very horny looking at sissy porn along with some of my favorite female pornstars who i feel really ABSOLUTELY LOOOOOOVE and really own stretching their not only beautiful but goddess-level and tight AF pussies that definitely got me to the slutty submissive masochistic level of horniness i reached after completely feminizing myself by shaving, doing makeup. fake lashes, lipstick, hair bows, goth girl lingerie and masturbating myself to orgasms at least 10 times looking through some well-put together sissy caption galleries that kept helpong me fantasize about being pushed to transition myself so i could be the slutty fem i feel like inside, getting degraded by dominant men who put me in my place by splattering me back to back with cum, making me eat as much as i can, reminding me to keep my flaccid 2in cock hidden in my cum soaked panties till they decide i can jack off onto myself then to think about how good it must feel to have a pussy as a woman, what all those sizes feel like, how long it has been since i stretched or got to feel something deep in mine because i no longer have parts of my toy sets, and most of all how much i would reallly love to one day be able to get creampied and feel cum matted in my hair, dripping down my face to mix with drool in my mouth, then dribble from my chin y
to my chest.

This black plug is about 6in tall with a girth of over 9in. My usual plug is at 6in girth and even that one has definitely got a painful stretch accompanied by that pop of your asshole triying to recoil back closed once you pass the lip of a plug but i had trained myself to register the pain from the pink plug's pop as something that makes me feel like such a submissive-bratty slut so i decided that since i was a little stretched out from leaving that plug in almost all day and night that i was going to take advantage and see how much pain i could could take and maybe get to take a humiliating picture of this plug filling my hole to a girth that is girthier than almost every dick on the entire planet. I found it very difficult to keep trying to go deeper but as i worked myself up and down, i fould that it started to change into pleasure that gave me chills like i was suddenly transported to a walk in refrigerator and the only way to get warmth was to fuck it with this animalistic instinct moving my hips up and down, making spiral patterns with my ass on each up and down motion. This inner slut spirit in me has clearly been depraved and the arousal i got from doing this for at least the next 20-30 minutes caused my limp tiny cock to pour q constant leak of precum pouring all the way to the floor way to the floor for about 15 minutes til i git up and decided to try every position i could to make my guts open up more inside. furthest i could get was about 1 inch from the bottom which made me feel so fucking desperate to be punished with the pain of it just popping in but it just kept hitting a dead end that would was pushing with such force along with the insane amount of lube i used that i knew if i let go, that it would pop out of me like i was a slutty sissy cum champagne bottle popping a cork 🤣😄😄 Thankfully i felt myself about to orgasm (my very first sissygasm actually because i did it all with just anal stimulation which basically bukkaked my stomach, it made left me so disoriented with prolonged waves of pleasure followed by trembles, but made me have to lay shamefully completely soaked in sweat, lube, and cum that didnt stop leaking out if me til around 7 mins after i had that orgasm hit. My asshole is was gaped for quite a while and i had to eventually strain kegels through my ass muscles to keeo myself from worrying about if i was leaking lube onto my floor.

I have never in my life felt so degraded, submissive, humiliated, pleasured, or more in tou h with the slutty trans girl i fantasize about being. Honestly I would love for the readers to keep that spirit foing by dropping some comments that degrade, humiliate, emasculate, and make me feel like im a dumb little slut who should keep trainig my mouth and ass further down the road of being a submissive sex slave cuckold toy to some dom goddesses or gods. wierd how addictive it is to dream about how badly it gets me off thinking about being a fluffer - voyeur for people who are obviously superior to give each other the sex they deserve while i experience that bliss of torture from denial and control. What can I say? im a hot mess who got the wrong biology for the girl i feel like inside.

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@confessions
15 Apr 2013 4:59AM
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i confess my neighbor is a sexy hot short tight big tit little girl ass milf and takes crazy amounts of sedatives while her husband is at work and when i work in my back yard i jump the fence sneak in her back door and always find her passed out on the couch wearing pajamas anyways she tells me later that she's a horrible sleeper and downs sleeping pills and alcohol and passes out and sleeps until 2 or 3 every day and she said how she sleeps so heavy her pet was actually fucking her or trying cus she was naked and she woke up covered in cum ... i was immeadiatley hard and excited when she said this so the next day and the last 3 days i've been going over there sliding her yoga pants down licking her holes and fucking them both and creampieing them both and leaving with her tits pulled out and her ass out her pants covered in cum and filled and i saw her all 3 days and she had no idea or doesn't care! never came harder in my life i tongue fuck her and fuck her ass so hard

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14 Apr 2023 10:16AM
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Odd thing happened last night. I went out for a beer with my coworkers, ran into my son and his friends. Small College town, it happens. His mom and I divorced years ago and I'm an active part of his life so it's weird, but not uncomfortable weird. Anyhow the whole group, me, co-workers, son and his friends... end up in this generational debate. Co-workers are Mils, son and friends are Gen Z, I'm the only Gen X. Lots of talk. Lots of banter. Lots of back and forth. 2 really cute Gen Z college girls start asking more and more about Gen X. They're my son's friends so I'm probably their parents age. Light flirting, lots of talking. Mil coworkers seemed semi jealous because they love attention but others filled that void. The two kept engaging me and it was good conversation. At one point she leaned in and whispered "think you can handle us?" I joke that'd I'd probably break her. "Not me" hugs her friend "Us?" I'm a bit stunned but the answer will always be yes. I track down my coworkers and let them know I've got a ride home. We get to the parking lot. She apologizes that her front seat is a mess. Student, lots of books. I end up in back with her friend. I rattle off the address and her friend leans in for a kiss. Car starts, clothes are sliding off, her friend gives amazing head. Empty house, not that it mattered, we went right upstairs to the bedroom. Kissing, fingering, touching, sucking, sooo much foreplay. The friend had a lipstick toy in her purse. She said she only used it solo... got them both off with it just because. We always made sure that everyone was teased at all times. If I fucked one, she ate the other. If one sucked me I fingered and ate the other. It took a lot to hold out, to make them go at least twice. The first time I went I was deep in her throat, fingering her friend who was massaging my balls. I pull out, they kiss, then her friend sits on her face and while she sucks out whatever's left. We just kept going. Didn't take long to grow again. Second time I went she wouldn't let me pull out. Balls deep. Her friend ate the creampie. Third time was a facial, her friend sat on her face right after. Not sure if anyone has fucked while girls 69 but it's so fucking wet and sloppy. We eventually just passed out. I showered in the morning. She woke up and joined me. I pinned her to the wall as I held her and fucked her. Pinched her nipple as she went. No mercy I felt how hard she O'd. I didn't go, and when she realized it she insisted on throating me. When we walked back in the bedroom her friend was lipstick toying. It was obvious she got off hearing us fuck. Not wanting to leave her out we fucked her even harder. I thought I'd be empty by now but I busted one deep in her. Literally felt the life draining out of me as I went. Cleaned up again. Headed downstairs to start breakfast. I walked past open doorways and passed out coworkers in various states of undressed. Some had women with them. A few were just passed out solo. Downstairs was a tangle of Gen Z, my son passed out on the couch, head in a huge chested redhead who was completely naked. One rule in my house, always has good beer, great bacon, and fresh eggs. People started waking up and moving to the smell of fresh bacon. Coworkers gave me a hard time when the first girl came downstairs and kissed my cheek. Jaws dropped when the second one did too. It was obvious by the way they walked and their bubbly attitudes they were still feeling great. Gen X doesn't play! I broke both of them. My son told me later it was kinda weird because he could hear both girls getting railed but it was mixed in the blur. Everyone was fucking in different rooms. He didn't realize I had a threesome until he saw them. Downstairs was a party, not an orgy, but he did bang the redhead on the couch. He promised he was safe. I didn't say a word.

Tests came back clean. Both girls were on the pill. Hell of a risk but they're fine. I was right. I'm 2 years older then their dads, and they've both heard their parents fuck so a chance to fuck a Gen X was a bucket list for them. I broke both of them. No excuses, no denials. I went too but they went hard. One swore she's never had multiple O's. I know I'm not the biggest. But damn they had fun. Very open, very sex positive generation.

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06 Nov 2014 4:59AM
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I confess that I recently stayed at a hotel near my work and on my second day there I heard a woman in the room next to me and immediately picked up that she was an escort working out of that room (heard her talking to a client on the phone). I got online and tried to find escort listed as working out of my area and could not find one that I thought matched the voice. I decided to slip her a note under the door playing it cool like I was just a neighbor that was looking to hang out and 420 if she was interested. I left my cell number on the paper and waited to hear something back.

After awhile I hadn't heard anything back and thought she probably found the note odd especially since I didn't tell her what room I was in, for all she knew I could have been LEO or something trying to get a response out of her, so I dropped another note letting her know what room I was in so she could feel more comfortable knowing the location of this mystery person that left her a note. After I slid the second note I went back into my room and rang her room on the phone letting her know that I wasn't looking to bother her but I left her another note in case she was interested in hanging out.

A little more time passed by and I get a text from her looking to smoke. I told her I would meet her outside and we could chat and smoke.

While smoking with her I started to offer her some other fun things a step past 420 and she said she was interested. After we finished smoking I brought her back to my room and was getting ready to give her some and I started to drop hints that I knew she was an escort. She admitted and I asked her if she would do something for me in return. She agreed. I handed some over and before I knew it she was on her knees with her tits out and began pulling my shorts down.

She gave me a long blow job with really good effort. It was probably about a 20-30 minute blow job, and as I was getting close to the end I was hoping I could cum in her mouth, but as I was getting ready to cum she pulled of and jacked me all over her tits.

I thanked her and she left the room happy (like me).

But here is where the real confession comes in:

A few days later (a few hours ago) I was sitting and work and decided to text her to see if she happened to still be at the hotel. She was. I asked if I could come by and see her again and she agreed. She told me she didn't have any rubbers though (as if she knew I had more in mind). I decided it was break time. This place is really close to where I work, so I walked there and picked up some rubbers from a gas station on the way.

I got there and I gave her about the same stuff as last time, with a little bit extra. Without a word she pulls the sheets down on the bed. I began to get undressed and went to lie down on the bed. She headed to the bathroom real quick and when she came back out I was naked on the bed waiting. She asked if I had rubbers and I told her I did. I got up and grabbed one from my pocket, and got back on the bed. She took off all of her clothes and climbed onto the bed with me.

She began with some light play, pecking at my chest and neck while rubbing her tits against me. I wanted to fuck her so bad that I was hard as a rock (usually need more foreplay, but I was ready to go). She looked down at my hard cock and reached to grab the cover from my hand, quickly opening it and sliding it on me, followed hastily by herself.

She climbed right on top of me and slid me in. She rode me for a good while, trying to get into it, but her riding game was not the best. After 10 minutes or so she climbs off and tells me to hit her doggy. I told her not yet and to turn around and ride me reverse cowgirl. She obliged. My view was wonderful and I was enjoying every minute of it. I grabbed her ass and began to thrust into her as I guided her ass up and down. After enjoying that for awhile I decided to hit it doggy.

Things got a little dry for a minute, but after a bit of standard doggy I began to push down on her, laying her flat on her stomach and lay myself more on top of her and began to hit is real good. She started to wet back up for me real good. I pounded away at her, feeling her wetness building more and more. I fucked her good and hard, making her cum on my cock. I enjoyed that and decided I really wanted to make her happy with my hard cock. My goal was to make her cum. A lot. I flipped her over for missionary and without a skipped beat was hitting her hard again, we were both breathing very deeply and I could tell she was really getting into it.

She was soaking wet and I found just the right spot and rhythm to put her over the edge again. I smiled to myself and just kept going. She was frantic in her breathing with barely comprehensible words of enjoyment sneaking out every so often between her breaths. I could tell she hadn't been fucked this good in a long time. She began to lose control and squirted all over making a big wet mess. Her face was super flushed and I could tell she was almost amazed at what my cock was doing to her.

I pounded away getting her to cum one more time before I was running out of steam. It was quite the work out and I was trying to decide if I wanted to push through it and work her into one final orgasm and cum with her (hindsight...). I told her I need a minute on my back and pulled out to let her climb on top. That is when she noticed the rubber was broken (that little dry moment before I took her to pleasure town...). She pulled it off and began to jerk and suck me off.

I wasn't thinking with the bigger of my brains at this point and thought to myself "I already fucked her with a broken cover... let's just keep going..." I was good and hard again and told her she should climb on it. She denied me saying the cover was gone. I told her I had another and went to grab it out of my pocket. She puts it on me and we get back at it. This is when I realized that while I was making her cum over and over that it was broken that whole time, because it wasn't feeling anywhere near as good with a new one on. I tried though, I thrust and I thrust and it just wasn't the same. I began to wish that I had just fought through getting a bit tired and plowed her into one last orgasm and came myself.

I would have creampied her, and the thought of that was the only thing my little head kept thinking. It didn't want the rubber anymore. It knew how much better it felt without it and it wasn't settling for less. After awhile I began to soften and told her I didn't thing it was going to happen "because of the rubber" she replied with "Yeah, probably... those things suck..." but she continued to refuse to fuck without one. At this point I knew I probably wasn't going to cum. The cover just didn't feel good enough, and I knew my mind wouldn't let me cum unless I was inside of her and she was cumming too.

She sure tried to make me cum though, She took the cover off and jerk and suck away. I'd say for about 30 more minutes... the whole time I had my eyes closed imagining myself blowing a load deep inside of her I kept getting close, but could not get all the way their. She knew I'd be close because I would get super rock hard. She was even getting some dirty talk in between having me in her mouth, but it Just wasn't happening.

I mind knew what my cock wanted and my mind, in an altered state of kinky and horny, was agreeing. Eventually I told her to stop. It just wasn't happening. I thanked her for letting me pleasure her and told her that I wish I could cum, but I probably wasn't cumming unless I was fucking her to orgasm again and I my cock was not agreeing with the rubber.

She understood, and we got dressed and went outside for a smoke before I took off. She had given me more time than I expected considering what I had donated to her, but I guess that is the power of a good fucking with a hard cock. She made a slight hint that next time she might let me fuck her in the ass.

I still wish that I came while fucking her missionary, exhausted or not. Pulling out from an intense shared orgasm to see a broken rubber and knowing I just came deep in her pussy would have made my day.

It may sound fucked up but I would have found it gratifying. Almost like I deserved it after fucking her brains out and making her cum all over my hard cock.

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10 Sep 2011 5:51AM
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I confess, that a few years ago, I was throwing a party at my house with my gf, now ex-gf. Well she asked if she could make out with one of our friends. I told her yes, because I knew the guy was a real stand up guy, and he would say no, no matter how drunk he was. Well she asked him if he wanted to kiss her, and just like I predicted, he said no. This frustrated her, and she told me he said no. I just laughed and said, that's the only reason I said it was ok, was because I knew he would.
Apparently, she took what I said as not only permission, but as a challenge, and I found out later, (I was busy DJing and playing bartender) that she made out with 2 other guys. I found this out as she was making out with a third guy, with her hand down his pants, jerking him off. Obviously, I got upset. She stopped jerking him off, but continued making out with him.
This made me upset, and I figured, if she did this, that I was going to get even, and started talking, flirting, and getting all touchy-feely with another one of our friends. She was into it, until she, brought up my gf. I told her what happened, and she said that she didn't want to be apart of a revenge thing and get on my gfs bad side. She did say that she did like me, and would like to have some fun with me, but not as long as I was with her. Fair enough, I didn't push it.
Another one of our friend's, we'll call her Sarah, drank way too much that night. Being it was a 3 bedroom house, but with 2 of the bedrooms being re-modeled, my gf helped her to the bathroom to throw up, clean her up, and then laid her down in our bed.
I knew about this, and claimed I was pretty drunk, which I was, but not wasted.
I went to the bathroom and then went to "go to sleep" Being we only had one bed in the only bedroom that was available, I went to lay down next to Sarah, who had passed out from drinking way to many Jager-bombs and several mixed drinks I had made her over the course of the night.
I laid down next to her, she was on her back, with her arms spread out. I laid down on my stomach with one arm under the pillow underneath her head, and my other arm around her cuddling her. She moved a little bit, but ultimately didn't care and seemed to smile with me holding her.

At this point I'll stop and give you a little description and background on "Sarah"
She was 22, 5'8", about 120lbs, she had curly brown hair with blonde highlights, lightly tanned skin, a real slim and toned, but still very soft body. She had nice B cup tits, just enough so you knew they were there, just about a handful, and very perky. She had a lovely flat stomach, not a six-pack, but very toned, and long toned legs.
She was wearing a low cut shirt, a pink victoria's secret, demi bra, and these tight blue jeans which accentuated her nice, small, but firm and round, ass.
One thing I liked about her, was that she was married, but was on a several month long break from her husband and starting to go to the process of a divorce, besides the fact that she needed some regular dick and would still go back to fuck him at least once a week.

Ok, so back where we were in the story. I took my pants off and laid down with her in my boxers and t-shirt and was cuddling her. I started to test the waters and lifted up her shirt some, and was going between caressing her stomach, her side, and the left side her back, with my right hand that was over her. She didn't seem to mind this at all, all she did was roll towards me a little bit, obviously liking what I was doing, and wanting to be closer to me.
I decided to push it a little further, and reached further up under her shit and under her bra to feel her tits and start to play with her nipples. This proved harder than I anticipated, because her bra was so tight. I fixed that, by pulling against me more, and reaching behind her, undoing the clasps on her bra. This gave me plenty of room.
I pulled her bra and shirt down a little bit, and reached in from the top. I started to play with her left breast and nipples with my fingers, rolling them back and forth, and occasionally giving them a little pinch. When I did this, I felt her move and looked at her face. Her eyes were still closed, but her mouth was open slightly, as she gave off a light moan.
Knowing that she was liking this, whether consciously or not, I decided to go a little further. I pulled her bra and shirt down even more, so her right breast was out of her bra. I slowly moved my mouth towards it, and kissed it, she didn't respond much, so I proceeded to suck on it a little more before moving to her nipple. I licked, sucked, and rolled it around with my tongue and lips. All the while, she started to moan slightly. I was getting kinda scared then, because how would I explain me sucking on her tits if she woke up. Luckily she didn't wake up as I proceeded to suck on her nice firm b cup breast.
I started to play with her nipple of her left breast with my hand while I had her right breast in my mouth and kissing on chest and neck. She seemed to enjoy this and was making a little bit more noise.
I figured if she liked this, she would like what else I had in mind.
I carefully unbuttoned her jeans, being sure not to wake her, I then unzipped them, giving me just enough room for the next step. I started caressing her stomach again and stopped playing with her breasts. From there I moved my hand down south and into her panties. It turns out she was wearing a nice lacy thong. I first cupped my hand over her vagina, not wanting to alarm her.
I then began to insert my middle finger into her and was pleasantly surprised that she was wet, apparently the nipple play had turned her on in her sleep.
I slowly ran my finger up and down her pussy. It was a lot tighter and smaller than I was used to with my gf. She was completely shaven, possibly waxed, because there was no stubble. She was smooth as could be. After making sure she was wet. I inserted my finger, up to the second knuckle, and damn was she tight. She started to breathe heavier, and fidgeted a little bit. I started to get worried, that she would wake up now, so I pulled my finger out. I cupped my hand over her pussy and let it rest there, under the guise, of if she woke up, I was asleep and just had it resting there. Ya not the best idea, but the entire time, my one defense was, that I was drunk and half asleep, and because it was it my bed, I "thought it was my gf". After a minute of resting, I started running my finger up and down her clit again and slightly grazing her clit, while rubbing her. I decided to move my focus there.
I started using one finger, and then moved to two. She was so wet and tight, and her clit was standing at attention. I slowly started to rub her. She started to breathe heavier, at this point I was getting scared and thinking she'd wake up, but she didn't. I started to rub her a little more, and her breathing got heavier, and she let out a slight moan. I continued to rub her clit, figuring if she wakes up, she most likely wouldn't care, because of the pleasure I was bringing her. Eventually her breathing got heavier, and she started to moan more. I continued rubbing her clit, until I heard her start to moan and saw her body convulse. I had made her cum while passed out. I put two fingers inside of her and pulled them out. I smelled them and tasted them. It was literally the sweetest pussy I had ever tasted.
This was too much for me, I had to get some release. Now with her tight jeans on, and only unzipped, there was no way I could come up with an excuse for taking her pants and while her panties were off, so fucking her was out of the question. I had to get creative.
Her pants being somewhat loose, I rolled her on her side away from me, and pulled her jeans and her panties down passed her ass. I then pulled my cock out from my boxers, which was so hard anyway from all that had been going on. I lubed it up with some of her juices left over from her orgasm. I then pressed it up against her ass and lower back, and started running my cock up and down her ass and stroking it at the same time. After a few minutes of this someone walked by the bedroom on the way out the front door to leave the party. I froze and moved my hand to my side, but we were so close that they couldn't tell if they looked it, I left my cock between her ass cheeks. and pretended I was asleep. After I heard the front door close, I waited for a minute, no noise anymore. So even though I was shaken, I still had to cum. I continued stroking myself while rubbing my cock between her ass and on occasion pointing it down and getting it to rub between the lips of her tight pussy and her thighs.
After a few minutes, it was more than I could take, I started humping her with my dick between her ass and my balls rubbing between the base of her ass and her pussy lips. I came so hard and filled her ass crack and lower back with my cum. I pulled my dick from her ass crack and pointed it down and squirted some more of my cum down her ass and on her pussy lips, soaking her panties in the process.
After I was all spent, I pulled her cum soaked panties back up and her pants as well. I sure wasn't going to try to button them or redo her bra clasps, but I put her tits back in her bras and shirt. I put my dick back in my boxers and wrapped my arm back around her, spooning her and holding her tight firm tummy, and tried to go back to sleep.
Before I could get to sleep though, my gf came upstairs and was ready to go to bed, she laid down and saw me cuddling with her, and rolled me over to cuddle with her instead. I pretended to be asleep/drunk and said oh, ok, and cuddled her and went to sleep.

The next morning, we all woke up, including some of the people who stayed over downstairs, and we all had breakfast and hung out more that day. Sarah brought up the fact that she thought it was odd that her pants were unbuttoned and that her bra was undone. She did not remember anything about that night after about the 3rd jagerbomb. All she knew was that her brother had put her in the bed early in the night, and then waking up in the morning.
The first thing anyone asked, was if I did it. I said no, that I was too drunk and went up there and passed out. My gf mentioned that I was cuddling her when she came to bed. I just went with the excuse, that I thought it was her, being so drunk, and just passed out as soon as I hit the pillow.
I brought up the fact that since I went up there hours later, that it was possible that she had undone them so it was more comfortable to sleep. She denied that, saying that she always sleeps in her bra, and never tries to take it off. She said that it looked like someone had just undone parts of her clothes to get at the parts they wanted to get at and have fun with her passed out. I started to get nervous, but played it off, and suggested that since it was a rather big party, that maybe someone at the party saw her like that and took advantage of her. She accepted that, but never went to suspect me, because I "went up there so drunk and passed out right away, and was so drunk that I thought she was my gf when I went to cuddle her."

She never did find out, in fact this is the first time I'm telling this to anyone, but it was a really hot night, and I totally get off on hot girls sleeping or passed out. I wish I had a chance to actually fuck her, but it would have been way to risky then. I almost got busted the day after.
One last thing, she never mentioned feeling any cum on her back or her cum soaked panties. She did get scared, not knowing what happened and bought a pregnancy test a few weeks later, but being I didn't cum in her, and only on her ass and outside her pussy, she wasn't preggo.
Part of me wishes I had got it inside of her and gave her a nice leaking creampie, but overall I'm glad I didn't, because of the headache it would have caused if she did get preggers, being she wasn't on any type of birth control.

I hope you enjoyed my story, it was all true, and a true confession from me. I'm not friends with her anymore, but did remain friends with her until me and my ex split up, and all the time I was around her, I couldn't stop myself from getting hard just thinking of that night.

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17 Nov 2020 5:45PM
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so last night i got very very very horny looking at sissy porn along with some of my favorite female pornstars who i feel really ABSOLUTELY LOOOOOOVE and really own stretching their not only beautiful but goddess-level and tight AF pussies that definitely got me to the slutty submissive masochistic level of horniness i reached after completely feminizing myself by shaving, doing makeup. fake lashes, lipstick, hair bows, goth girl lingerie and masturbating myself to orgasms at least 10 times looking through some well-put together sissy caption galleries that kept helpong me fantasize about being pushed to transition myself so i could be the slutty fem i feel like inside, getting degraded by dominant men who put me in my place by splattering me back to back with cum, making me eat as much as i can, reminding me to keep my flaccid 2in cock hidden in my cum soaked panties till they decide i can jack off onto myself then to think about how good it must feel to have a pussy as a woman, what all those sizes feel like, how long it has been since i stretched or got to feel something deep in mine because i no longer have parts of my toy sets, and most of all how much i would reallly love to one day be able to get creampied and feel cum matted in my hair, dripping down my face to mix with drool in my mouth, then dribble from my chin y
to my chest.

This black plug is about 6in tall with a girth of over 9in. My usual plug is at 6in girth and even that one has definitely got a painful stretch accompanied by that pop of your asshole triying to recoil back closed once you pass the lip of a plug but i had trained myself to register the pain from the pink plug's pop as something that makes me feel like such a submissive-bratty slut so i decided that since i was a little stretched out from leaving that plug in almost all day and night that i was going to take advantage and see how much pain i could could take and maybe get to take a humiliating picture of this plug filling my hole to a girth that is girthier than almost every dick on the entire planet. I found it very difficult to keep trying to go deeper but as i worked myself up and down, i fould that it started to change into pleasure that gave me chills like i was suddenly transported to a walk in refrigerator and the only way to get warmth was to fuck it with this animalistic instinct moving my hips up and down, making spiral patterns with my ass on each up and down motion. This inner slut spirit in me has clearly been depraved and the arousal i got from doing this for at least the next 20-30 minutes caused my limp tiny cock to pour q constant leak of precum pouring all the way to the floor way to the floor for about 15 minutes til i git up and decided to try every position i could to make my guts open up more inside. furthest i could get was about 1 inch from the bottom which made me feel so fucking desperate to be punished with the pain of it just popping in but it just kept hitting a dead end that would was pushing with such force along with the insane amount of lube i used that i knew if i let go, that it would pop out of me like i was a slutty sissy cum champagne bottle popping a cork 🤣😄😄 Thankfully i felt myself about to orgasm (my very first sissygasm actually because i did it all with just anal stimulation which basically bukkaked my stomach, it made left me so disoriented with prolonged waves of pleasure followed by trembles, but made me have to lay shamefully completely soaked in sweat, lube, and cum that didnt stop leaking out if me til around 7 mins after i had that orgasm hit. My asshole is was gaped for quite a while and i had to eventually strain kegels through my ass muscles to keeo myself from worrying about if i was leaking lube onto my floor.

I have never in my life felt so degraded, submissive, humiliated, pleasured, or more in tou h with the slutty trans girl i fantasize about being. Honestly I would love for the readers to keep that spirit foing by dropping some comments that degrade, humiliate, emasculate, and make me feel like im a dumb little slut who should keep trainig my mouth and ass further down the road of being a submissive sex slave cuckold toy to some dom goddesses or gods. wierd how addictive it is to dream about how badly it gets me off thinking about being a fluffer - voyeur for people who are obviously superior to give each other the sex they deserve while i experience that bliss of torture from denial and control. What can I say? im a hot mess who got the wrong biology for the girl i feel like inside. [s][s]

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mollythedeviant
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30 Apr 2013 2:20AM
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Dream come true... you know how sometimes friends of the family have kids you grow up with? like your mom's best friend who insists you call her auntie? Her kids. Nick and I grew up as cousins. Couple years apart, but pretty much in the same age group. Granted, we were teenagers at the time. We weren't super close or anything. I was closest to his sister, actually. Anyway. We'd hung out a few times in high school and in college. Smoked out. Whatever. together. Whatever.
There was a wedding in the "family" this weekend. He flew out from cali, and I drove a few hours south to meet them all. I didn't know he was going to be there. I was there for his sisters to hang out and help out with photography and such. When we were introduced and realized we knew each other, we were a little shocked and surprised to see how the other had changed. It had been at least 6 years.
After the rehearsal dinner, we all got pretty faded. But then the fucking hotel overbooked, so we all had to share rooms. Shit you not. Two queens. 7 people. Per room. We did shots at the hotel room. He kept offering me more. Quarters were tight. Every time he passed me, he placed a hand on my shoulder, or brushed up against my hand. I suggested we all go down to the hot tub before it closed. None of us brought swimwear, so we were all in our underwear. To my alarmed disappointment, he didn't come near me. Afterward, we all took turns showering and changing into our sleepclothes. It was a hot day, and 7 people in a room didn't help. So we were all pretty mych in teeshirts and panties. While some were out getting ice, getting more towels, and showering/blowdrying, he crept up behind me with a wet towel and cracked it on my thigh just beneath my panties. I smirked at him, and he admitted that he was impressed that I didn't flinch. I locked eyes with him and said "you have no idea..."
Not much later on, after a few more shots, he came and me and whomped down on my ass with a firm, open hand. Once more I locked eyes with him with almost a warning glare. Later that night he said he would go out for a smoke with me, but it was getting late and there was a wedding in the morning, so he passed out. I couldn't sleep the whole night. My mind was racing. Hoping he would creep over the slumbering bodies and grope me. Maybe signal for me to follow him out to the car.
He never did.
After all the festivities and we returned to our hometowns, I texted him and asked him if I was imagining things, or if he had touched me quite a bit.
He admitted to being a little feely. At first he started to blame it on being drunk. And then he confessed he was intrigued by the way I took a spanking. We shared kinks back and forth until the conversation reached incest. And he confessed to being turned on by staring at a married cousin's ass. By wanting to beat it. By wanting to forcefully grope it. By wanting to fuck it.
Ladies and Gentlemen. (Okay, mostly dirty men.)
My "Cousin" is now my sext/skyp Master. He calls me a whore, and reminds me of how filthy I am for showing off for my cousin. He even has an uncle he wants to whore me out to, (different family...) and that he's open to sharing a pet. I gagged on my dildo for him on webcam while he told me how much he wanted to forcefeed me creampies. I have officially hit the jackpot. I'm so excited!

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