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11
Anonymous
@confessions
13 Apr 2015 8:54PM
• 2,604 views • 0 attachments
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I like trannys. I love the taboo of lifting up a skirt, seeing a dick and the sucking it.

Saturday night, being alone, horny and bored I surfed the casual encounters section of Craigslist under T4M. Found a tranny in my area who was looking for a no strings attached hook up. This one was also a VERS (top and bottom) and that was something I had been wanting to experience. Wasn't sure if I was ready to get pounded, but I at least wanted the option.

I got there, was invited in and as we talked, tranny told me that there was a spouse. I was nervous at this point and that said spouse was home. I was nervous. No advanced warning, I wasn't exactly quiet. The marriage is open and the spouse was told that I was coming over and why. So I was a bit calmer. Then I was asked "Do you want to meet my wife?" I wasn't expecting that question, but I agreed because I know some people in an open marriage want their spouse to meet their fling as a sign of honesty or something.

She entered the room and come to find out, the spouse was another male to female tranny. That was also unexpected, but what ever. So the three of us talked, then the spouse asked "Aren't you here to fuck my wife?"

I answered "Yes, I just was waiting for you to leave."

"You think you two are going to have sex and I get nothing?"

By this point my dick was about to tear through my pants. I thought she was still screwing with me, but part of me knew she was serious. I was about to ask another question when she said "Either get on with it or leave."

That's when I felt a pair of lips on my mouth. The tranny I met on line and I started kissing and undressing each other while the spouse watched. I have been watched before, but those were times when I was having sex with a woman. Here someone was watching me, and stroking themself while I sucked a dick.

This was suck a turn on that I came while I was on my knees. I was rubbing myself while sucking and getting dick slapped. I wasn't ready to be done just yet, and neither were they. I stood up and was ordered to bend over the arm of the couch. I watched as the tranny picked up the bottle of astroglide. Her spouse was now in just a bra. Her nightie was removed sometime before and her dick was in her hand. She was passable transvestite, no hormones, perfectly working dick.

I felt the dick head against my asshole and slowly my asshole opening up to accept it. I was getting it, my first time, bareback. My dick was hardening again.

I felt the dick slide out of me and felt the cum on my back. I then looked up to see the spouse come towards me, stroking her dick. I watched as she came over my face.

I laid on the couch, stroking myself as they watched. I asked them to call me a "cum covered faggot", and as they did I came on their floor.

I drove home in a bit of shame...and still get hard thinking about it.

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6
Anonymous
@confessions
08 Jun 2012 6:41PM
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Having a sexual relationship with family members can
get started in just about any variety of situations,
some because one or more member has the definite hots
for the other, and some because of circumstances that
arise almost out of nowhere. Mine arose simply because
of my sister, and what she did with her birthday
present.

Darla got a small, hand-held video camera for her
birthday. It was pretty neat, and she went around
videotaping everyone in the house. I didn't know that
she had videotaped herself, too, and what she was doing
while she taped herself.

"Come on, Gary, let me show you my tape," she said.

"I've seen your tapes all day," I said. Mom and Dad had
gone to bed, and it was late, and I was tired. It was
past midnight.

"No, you haven't seen this one. I guarantee, you'll
like it."

I followed her to her room, where she hooked up the
small camera to her TV set.

The tape began in her room, with her just standing
there smiling. She sat next to me on her bed, and then
she nudged me. "Here's the good part,Gary."

She was laying on the bed, her legs spread, her fingers
moving up and down her pussy lips. I could feel my cock
suddenly grow, and I knew that my face was getting red.
The room suddenly felt stuffy.

She writhed around on the bed, rubbing her pussy,
lifting her skirt higher andhigher. Then, the tape
showed a close-up of her red, swollen pussy lips. Her
fingers moved to her cunt, and she pulled her lips
apart, rubbing her clitoris.

"Do you like that, Gary?"

I didn't know what to say. "Yeah," I said. My voice was
choked.

I squirmed, trying to adjust my hard-on in my pants. I
had never imagined that my sister looked so good. I
mean I knew that she had a nice body and all, but to
see it on display like this was giving me all sorts of
ideas.

She reached over and put her hand in my lap. Pressing
downward, and looked at me. She pulled my hand from my
side and put it on her knee, then pushed it up higher.
I could feel her smooth thighs and the warmth of her
crotch as she pressed my hand up under her bath robe
against her pubic bush.

I gently moved my finger against her pussy, feeling the
downy hairs beneath my fingers. At the same time, she
was rubbing the outline of my hard cock through my
pants. I felt her fingers on my zipper.

"Take off your clothes, Gary," she murmured. "I want to
take some more videos."

I knew that what I was doing was probably wrong, but I
had no choice, my hormones were raging at this point so
I stood and took off my shirt. She reached up and
unsnapped my pants, pulling them down to the floor. I
stepped out of them as my hard throbbing cock jutted
out over the band of my briefs.

My sister gasped audibly. "Damn, Gary,
you've got a big one!"

She reached up and grabbed my cock and pulled me toward
her.

She held it in her hand, examining it closely. With her
other hand, she tugged at the band of my briefs, and
pulled them down. As the elastic band passed over my
hard cock and set it free, it popped back up in the
air, reaching all the way up and slapping me in the
belly below my navel.

She stood and pulled off her robe. She wasn't wearing a
bra. Her tits bounced provocatively as she sat again
and pulled my cock to her face.

I watched with fascination as my sexy sister put her
lips around the shaft of cock. She ran her lips up the
length of it all the way to the head. Her tongue darted
out, flicking out and swiping across the purple head of
my rigid dick.

She then slowly moved her mouth down again, licking my
cock all the way to the base of it, holding my balls in
her hand. She pulled my heavy balls to her mouth and
licked, then sucked one of my swollen orbs into her
mouth. I couldn't believe that she was doing this, it
was like a dream.

I pulled away from her. "Lay on the bed," I said.

She lay back and spread her legs. "Please, Gary, fuck
me," she whispered. I didn't need to be asked twice. I
climbed on top of my sister, sucking on her erect
nipples as I positioned my cock against her hot, wet
pussy. I felt her reach down and guide my cock, wiping
the head of it against her juicy pussy.

I pressed gently, pushing my cock inside her a little
and she moaned. I thrustall the way into her, feeling
the warm, moist tightness of her cunt. I could feel my
balls pressing against her ass and she moaned again. I
began to thrust in and out of her with a rhythm she
seemed to like.

She tightened her legs around my ass, as her legs began
to tremble and shake. She moaned, and I could feel
spasms in her body as she pressed against me. Then she
came, just as I felt my balls tighten. I shot my cum
deep inside her, filling her hot box with my own
sticky, hot juices. I couldn't have held back if I'd
wanted to. It was like she was sucking it out of me.

After a few minutes, I pulled out of her and lay beside
her on the bed, dragging my cock across her legs,
leaving a sticky trail of cum and cunt juices.

"Why the hell did you tape yourself, anyway?" I asked.

"I wanted to see what it looked like."

"Looked pretty damn good to me," I said.

"I wanna see what you look like, jacking off, or
something."

It was that "something" that we taped.

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9
sick_o
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@random
08 Mar 2015 4:20AM
• 6,356 views • 0 attachments
[ − ] thread [ 6 replies ]

Craigslist Story #1

So I've been using craigslist for about 15 years and started using the hook up section about 13 years ago and I'm still going strong! Let me tell you about my first casual encounter.

I was browsing through the casual encounters like I had been doing for a while and finally decided to answer an ad looking to get their cock sucked. The pic in the ad was a nice looking average sized dick with a pretty straight forwardly written ad, he wanted his cock sucked by another dude. I was in the mood and sent him a response, almost immediately I had a new message in my inbox! He sent me his address and I told him I was on my way. I get up and grab my jacket and cellphone and run right out the door to my car. I hop in my car and hit the highway. He lived a city over up on the hill or at least that what was the address told me. I drove for about 15 minutes then hoped of the exit and up the windy roads until I reached the house.

I pulled into the driveway of this massive modern mansion built into the cliff, it was pretty fucking impressive. I turned the car off and pulled my phone out of my pocket and put my earpiece in, it was corded one that went in a single ear. I look down and dialed this chick I had met on AFF the month before, she a massive 375lb disgusting whore of a woman, I really miss her... Anyways the phone begins ringing and after only one ring she picks up the phone but before she even says hello or what's up instead she says... "Come fuck me". My response was just as classy... "Shut the fuck up and just listen", She asks "What?". What I MEANT WAS "I cant talk so just listen to what's about to happen". I explained myself better just as I was opening my car door and immediately she asks me "Are you going to suck some cock? Please tell me you're going to suck cock ( )". I tell her "Ssshhh, just listen", I step out my car and shut the door. As I look up there is a man standing at the gate staring at me, so I stuff my phone into my pocket and walk toward him. Just as I get in earshot of him he says "Nice car, you must do well for yourself", at the time I had a pretty swanky ride. I answered with "I do ok, you must do pretty good by the looks of this place.". The guy smiled and tells me he is just house sitting for a fiend. I follow him into the house and he shuts the door behind us...

As he leads me to the lower level of the home the chick is in my ear talking up a storm saying shit like "Oh my god ( ) you're going to suck some cock" and "Swallow all his cum", she was so turned on. As I get to the lowest level where I'm about to put this strangers cock in my mouth I look up and see the entire wall facing out toward the urban sprawl at the bottom of the hill is a giant panoramic window. I turn and walk up to the window and take in the view but when I turn back around I see him sitting on a couch facing me he has opened his robe and has his rock hard cock out. I walked right over and got on my knees without saying a word! I leaned in and slid his stiff cock into my watering mouth and he immediately let out a moan which the girl on the other end heard sending her overboard. She loses it and starts rambling aggressively "Suck that fucking cock! Take it all" that gets me salivating hard as I bob up and down on his cock deeper, wetter and faster. All this causes the guy to start gyrating his hips and trying to fuck my mouth as moans and says "Oh my god you have super head". That pushes me over the edge... I pull back a little and grab his cock with my hand then slide it out of my mouth so that the head is barely touching my lips, I'm staring him in the face but his head is leaned back.

Well he must have felt me looking at him because he looks down and our eyes lock. I get so turned on that I grit my teeth and tighten my lips as I let out the most nasty, disgusting, filthy growl just before I lower my lips and start licking and sucking on his balls. Without breaking eye contact I move back up to the head of his cock while I still have his shaft in my tight grip. I clench my mouth tight again and slap myself on the lips with his stiff piece of meat a few times. He moans and I let out a deep breath then slide it back into my mouth almost taking it all down. At this point my friend sounds like a cheerleader at a high school football game, she is going crazy and can't stop cheering me on but in a disgusting sexual manner... Which gets me going harder. I must have been bobbing up and down on his hard cock for five minutes straight when he begins wiggle and thrust his hips, just then in a loud moaning voice he spits out "Oh, I'm going to fucking cum.

She hears that and her voice drops real deep and she talks through her gritted teeth... "You better swallow all that cum! Don't waste a single fucking drop" Just as she says that he grunts and I feel the first warm spurt in my mouth and I let out the loudest, deepest groan that I possibly could with a cock in my mouth! I grab his wet slippery cock with my hand and slide my mouth up to the head as I start jerking him while I suck the his hot cum right out the split in the head of his dick. I drink down his hot, salty jizz while my friend listens in bliss on the other end of the phone. I suck out every last drip then pull my mouth of the head of his cock and squeeze the tip getting a small drips worth off cum to surface... I lick it up and say thanks as I stand up to leave. He looks at me and says "that was amazing". I make my way to the stairs and he hops up closing his robe following me up the stairs. As we reach the door I open it and he grabs it by the wood holding it, I turn toward him and all in one motion I reach into the robe and grab his semi erect cock giving it one last stroke as I say "Thanks" then turn and walk out.

I go up the driveway and get in my car its so quiet I forget I'm still on the phone with my friend. She blurts out "That was hot!" and I say "You're welcome" jokingly. I start the car and back out the driveway then head down the hill. Before I reach the bottom of the hill I tell her to jerk off so I can listen, without a single word spoken I can hear her breathing heavy and moaning. When I get to the bottom of the hill at the stop sign I immediately get my pants down enough to get my big hard cock out and without letting her know begging jerking off. As I head toward the freeway I'm stroking myself slowly but once I get on the highway I start stroking hard and fast as I fly down the road. It's about 2 am on a weekday so nobody but me is on the highway and I'm zoned out listen to her jerk off and trying to drop a load myself. She is moaning like crazy and I'm getting close myself. I feel it coming so I start stroking like mad and out of nowhere she say says "Fuck yeah! Come for me ( )", she knew I was jerking off. I'm on the verge of squirting a huge load so my focus is only on my dick and the road in front of me. My cock is tingling and I feel the cum rising into my shaft ready to spray everywhere. I can feel that there is a car next to me at this point and they are keeping pace, I feel there eyes on me but I don't give a fuck because I'm ready to cum. Just then the tingle hits the head of my cock, I let out a growl and yell at the top of my lung "I gonna' fucking cum" and the first spurt of hot seed sprays out...

It is a huge thick stream that comes right at my face! I spray myself right in the face and over my head. The second is another fat rope and straight in my face again. I feel the third come out like a puddle of water all over my hand... The wetness does it and I let go and start licking the cum off my hand like the sexual deviant I am! I can feel the eyes of the person in the car next to me and I smile knowing I gave them a hot show. I mumble "Fuck yes" and my friend says "That was hot", I say back to her "You know what's hotter?", "What" she says... "The person in the car next to me just watched my cum all over myself", "Really?" she says. "Fuck yes" and I turn to look at the person driving the car and its a fucking ******* patrol... I turn white as a ghost and he slows down then gets behind me and hits his lights. I say "oh shit" out loud which gets my friends attention. She ask what's wrong and I tell her it was *** watching me and he's pulling me over now. The first thing out of her mouth is "Tell him you'll suck his cock", I tell her to shut the fuck up because its not funny, I'm going to go to jail. I throw my blinker over and cross the lane to my right to pull on the shoulder. He comes on the speaker and says...

"No! Pull off the exit up ahead"

To Be Continued...

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7
Still_Anonymus
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@confessions
29 Apr 2017 11:14AM
• 2,292 views • 0 attachments
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So as requested via poll, here is the Patty story. Next will be Haley and then continuing with Anna :)

Part12: Patty [look up the other parts on my profile :)]

As you could guess from the wedding episode, Patty is a bit slutty. After the wedding I thought I had heard the last of her, but I should be proven wrong. While Jim and Anna were on their honeymoon, I was watching over their house, getting the mail, watering the flowers and so on. Patty (now 20 yrs) was texting me, just two days after the wedding:
P:"Hey there ;)"
Me:"Hey... I didnt know you had a boyfriend..."
P:"I know, I never told you."
Me:"So... are you guys in an open relationship? does he know?"
P:"No and no. And it would be better for all of us if he never found out."
Me:"Well okay... do you do that often?"
P:"What? cheat on my bf? Lets just say its the first time with this one..."
Me:"Why do you do it?"
P:"I dont know. I guess I need more sex than Brian can provide. I really dont understand how Anna could stay faithful to Jim, even though their sex life is so boring..."
Me:"Okay... what I still dont understand is, why are you texting me about all this?"
P:"Well I honestly didnt want to talk about that... I just wanted to know what you are doing?"
Me:"Well I was just going out to water your sisters garden."
P:"Oh so you're watching the house for her?"
Me:"Yep."
P:"okay :) gtg now, see you soon."

I went over to Annas house and started watering the garden. When I was almost done, I heard the gate to the garden. Me:"Hello? Who's there?" When there was no answer I went looking. There are some bushes next to the gate and when I approched them, Patty jumped out and scared me. Me:"Woah what was that?"
P:"Wow you really jumped at that."
Me:"That wasnt funny..."
P:"I think it was."
Me:"What are you doing here anyway?" She was wearing a trench coat.
P:"Well I have a surprise for you..." with that she opened the trench coat. She was naked underneath. I couldnt believe my eyes.
P:"Speechless huh?"
Me:"Yeah... Do you really think this is a good idea?"
She went on her knees and pulled down my pants.
P:"Do you think it is?" Then she started sucking. She got me hard in seconds. I started pulling her hair, she loved it. After I was rock hard, I turned her around and kneed behind her, on her trench coat. I slapped her ass and said "you're a real slut you know that?"
P:"Keep spanking me...yeah..."
So I did. I spanked her, till her ass cheeks were red. Her pussy was already wet when I started playing with it, so soon I was pushing into her.
P:"Oh yeah your dick is so big..."
I was already fucking her fast and deep, but when I started choking her, she had her orgasm. Her legs gave in and she laid flat on the chest. I wasnt done though. I repositioned and kept fucking her.
P:"Oh yeah keep fucking me... use me..."
So I held her head down while fucking her pussy sore. I soon shot my cum into her pussy. When I pulled out, she turned around and I stuffed my dick into her face. She sucked it willingly till the last drop of cum was gone.
We got up and dressed.
Me:"So I guess this will not be the last time you will be here, am I right?"
P:"Right."
Me:"How are you going to hide that from Brian?"
P:"He's not the smartest guy. I'm just going to tell him I'm meeting with a study group. You sound so negative. Dont you like fucking me? Do I not turn you on?"
Me:"Its not that. You are beautiful. I like the sex very much. I just dont know if cheating on your bf all the time is such a good idea. Also I'm very close with your sister... what will she think?"
P:"She will never know."
Me:"Okay, but if she shall never know, we shouldnt go on with this beyond her return."
P:"Deal. Do you think I look a lot like Anna?"
Me:"Yeah, kinda..."
P:"So do you think of her while fucking me?"
Me:"Umm... no..."
P:"Do you think she is sexy? Or beautiful?"
Me:"Well... yeah but..."
P:"What but? Would you fuck her if you could?"
Me:"No... I dont feel in that way towards her..."
P:"Okay okay. Well... when will we meet the next time?"
Me:"Well I only water the plants every 2-3 days."
P:"Okay, do you have snapchat by the way?"
Me:"Well yeah..."

After that we would fuck every 2-3 days, and in between I would sometimes get snap chats from her. They turned out to be very helpful, when Anna didnt believe me, that Patty fucked me with she was away.
The next few times we always went to the house to fuck. It turned both me and her on, to fuck in her sisters house/bedroom. We also would fuck in the kitchen once or twice. When the last day before Anna's return came, Patty and me were in the bedroom again. During foreplay, Patty asked me to finger her butt. After I fucked her in missionary for a while, she turned over and said "I wanna try anal with you. Brian would never do that with me... but I wanted to try it for a long time.."
Me:"Do you have some lube?"
Patty handed me some. I put some of it into her and some over my rock hard cock. I started fingering her ass again, first with just one finger then with two. With those two I streched her ass a bit. When I put in the third, Patty sharply inhaled. I stopped for a second, but she said "go on... I want your dick inside my ass..."
My dick was still too big for her ass, so I went slow. Bit by bit I was able to push in further. When I was all the way in, Patty was breathing heavily.
Me:"Are you okay?"
P:"Yes.. Yes. Just start fucking me already..."
I moved slowly at first, but soon I was pounding her ass. Her moans were screams at the same time. My left hand was playing with her clit.. her pussy was soaking.
P:"yeah just like that... just like that... uhhh... I'm cumming... I'm cumming!"
I pressed my hand against her pussy so I would catch most of her juice, but I didnt stand a chance against her waterfall. So Patty's juice was dripping on Annas bed. That thought turned me on so much, I came instantly. After I had filled her ass, I pulled out and she said "Damn you just destroyed my ass...I love it..."
Her pussy was still dripping, and now her ass too. She went to the bathroom and I cleaned up some of the mess we made. After we both got dressed, Patty said:
"Well I guess this is goodbye. Dont forget: no one can know about this."
Me:"So you wont even tell Haley?"
P:"Correct."
Me:"Well I'm gonna miss your snaps I think..."
P:"Well... I can send you more... if you promise to fuck me in the ass from time to time..."
Me:"I think I can do that." We laughed.

After that I didnt see Patty for years. She sent me some more pictures, never asked me for another round though. After some months Anna told me that Patty had a new boyfriend. Around that time the contact broke off completely. I have seen her lately though, but thats a story for another time :)

End of Part 12

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Anonymous
@confessions
18 Dec 2025 12:05PM
• 248 views • 0 attachments
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The best advice I ever got about marriage and sex came from this board. 

It worked. Like really worked and our relationship has never been better.

I laugh when I see just awful "expert advice" from other so-called reputable sources that isn't this. 

You guys were *right*.

For any other men struggling with your wife or girlfriend and not getting what you want from sex or sex at all:

Stop being a bitch and go fuck the shit out of her. Make her do what you want. Do not hesitate, no half measures. Literally pick her up, throw her down, tear her clothes off. If she protests as if she's too shy or it's not a convenient time, keep going. You'll know a legit hard stop when you hear it...but you won't. Push through the "you're messing up my hair" nonsense.

Do what you want. Throw her legs open and lick her pussy. Shove your dick in her mouth. Fuck her tits. Put her in whatever position you want. Pound her doggstyle and pull her hair. Direct her. Tell her what she should do. Slap her ass. Fuck her ass. Whatever you feel like. And when you're fucking her, no gentle stroke bullshit. Thrust into her- hard. Make her feel your dominance over her with every rep. Pin her wrists down. Squeeze her tits. Doesn't matter- just pound *hard*.

When you get to the point of no return, pull out and cum on her face. Don't ask, don't warn, just do it. Grab the back of her head, pull it towards your cock and nut on her face. She might hate it but if you've never done it- just do it. (She may say never again, but you can figure that out later.)

This advice gets shot down all the time by people who have never actually done it. It's too rough. It's degrading. Whatever. She's your wife. Chances are she's into everything you are, you were just too scared to try it.

I finally sacked up and did exactly this. She protested a bit at first but got into it within about a minute of understanding I wasn't playing around. Picking her up and throwing her on the bed shocked her. She tried for a second to resist me pulling her legs apart to lick her clit and it was all over after that. Zero resistance. Total compliance. Didn't care at all that she had cum dripping off her face afterwards. Just total brain melt from being used like that. For hours and days afterwards. She *loves* it.

We can't keep our hands off of each other. The sex is amazing and we get along with each other so much better. This has leveled up marriage more than anything else we ever tried. She needs to be used. She was too afraid to ask and I was too afraid to try. 

Don't be a little bitch like I was being. There's a high probability your wife wants to be taken like this, too. Go do it. Stop fucking thinking about "what if". Stop listening to people who've never actually tried it. Just make it happen.

Good luck. 

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