Heres my confession....
Ive always had this thing for anal sex...Freudian psychology and his bullshit may play a roll but I was never touched or done wrong as a child, anyway...

The first time I had anal sex was with a girl in College...she really didnt like giving head but she loved sex..so one night in a drunkin talk I told her I wanted to stick her in the ass, she would be my first...she replied "its been a long time!" lol yeah right bitch you in college fucking everybody lolol... She agreed and I grabbed some "baby oil" lol...I was still using comdoms at the time so I gently proceeded to put myself inside of her...she moaned low and deep until it was all the way in :-) I started to stoke her gently as she told me to not go to fast. Soon after about 5 mins her asshole was open enough to pound!!! I absolutely loved it!!! Of course I came and that was it :-):-):-)

Alight so the next time we linked I told her I wanted to do it again she agreed but this time half way thru the anal session the condom broke. I felt it immediately but I couldn't stop myself...I kept going and it felt so so so so so so good. And actually before this point in my sexual history I had never raw sex..only protected so this sensation was very new :-):-):-):-):-):-):-)

Okay now here is my true confession....A few years later, I had sex with a chick and she was used to anal sex. I trusted her so I proceeded in her raw...about 15min later I looked down at my dick and it was becoming brown...at first I wanted to stop because I started to smell the odor but then I found myself not able to control myself...I LOVE DIRTY ANAL SEX!!!! ITS JUST SOO RAW and NASTY. I LUV I LUV I LUV....I begin to fuck her harder and harder harder and busted a big ass nut in her ass. She then bent over and pushed it all out...I almost fainted from excitment!

My Confession!!!

I know some of you won't believe me. But there are some decent looking pan-handler chicks out there. And some day once in a great while you may find one that is kinda hot.

Let me clarify, I live on the West so there are these young people usually between 16-20 that are like hippy urban backpackers, or "gutter-punks" (google it). Basically runaways.

Well, I've never done anything even remotely like this before but I've always fantasized of taking advantage of some slut.

My confession is that I was driving to WalMart and standing in the center divide was a shapely asian girl wearing tight pants and a little shirt showing off her mid-section. She had a cardboard sign that said "Anything Helps".

Her face was decent and she didn't look that dirty, but her hair was kinda matted.

I stuck my hand out of the window with a couple of quarters and she came down the line of cars to get them.

When she took them I smiled and said "Blowjob?"

She looked away and then down, but it didn't take her long to respond. I looked to make sure the light was still red and she said, "20".

I unlocked the passenger door and she got in.

"Let me see the money"

"I have to go to the ATM, I didn't expect to see you."

She agreed to go with me and we made small talk about how long she had been in town and I some how got her to agree to suck it first and then we would go to the ATM.

I didn't get the impression she did this sort of thing. Maybe I was hr first paying customer?

Certainly not her first blowjob.

We parked in the back of a near by strip mall where 2 out of 5 stores had closed down (a sign said 99 cent store coming soon).

I took out my cock and she looked like she was having second thoughts for a moment. I smiled and she put her mouth on it.

She was just kinda doing an OK job but it was a hot scenario and I was already hard.

After a few minutes of letting her do it herself but not really getting close to cuming, I started to pump her mouth, not too long into that she wasn't keeping her head down so I forced her down into my crotch as I pumped her face. I could hear her gagging and she started to buck but I said "I'm almost there, hang on" and she relaxed a bit, gasping.

It was about a minute of this, her bucking and making a "glub glub" sound with me holding and pumping hard into her mouth that I came.

She made no attempt to swallow and my pants we all slimey with a mixture of drool / spit and cum.

When she came up, her eyes and nose were red like some one that was just crying really hard.

I said "That was good", relaxing from the release of my load and still hard.

She, wiping her mouth with the sleeve of her jacket said quietly "you're an asshole"

I said "you did a good job"

She leaned back in the chair not looking at me and just said "fuck you" pouting.

I was still hard but it was going down and I decided to put my cock away, grabbing some left over fast-food napkins to wipe up her drool mess on my pants.

While I'm doing this she said "I want my money now"

Now, when I picked her up I had full intentions on paying her but when the thought crossed my mind to gyp her out of it, my dick instantly became hard again.

I smiled and said "I don't have my wallet".

She got pissed at this point and was all like "what the fuck, I fucking hate you" saying she was dumb and should have known better, kinda was crying, so I gave her the rest of the change in my cup holder which was mostly pennies but some dimes and quarters - at the very most 5 or 6 dollars but it could have been only 4.

She looked at me with such spite after I emptied the cup of change into her hand, some of the coins were sticky with soda and there was a paperclip and some dirt and a couple screws.

I said "thanks, it was good" and she just opened the door and said "fucking asshole" quietly.

From there she walked off.

The sun had been going down and now it was late. Too late for her to panhandel any more that night.

I drove away and just saw her slowly walking through the empty back parkinglot with her head down. My guess is she's sleeping in the little hutch with the dumpsters behind the store tonight.

Am I a bad person?

When I was 19 years old and in college in Florida, I got really heavy into drugs. Mainly party drugs like coke and ecstasy, and of course plenty of weed, but on occasion other drugs as well. I was out of control and living one big party life on my parent's dime while they struggled mightily to pay for me to have the opportunity they never had and go to college. Looking back I feel like a total asshole about it now as they wanted nothing more than for me to be successful and not have to struggle...sorry, I digressed.

Anyway, since I had no money and wanted to keep up my partying lifestyle and since I was always very athletic, in shape and considered "good-looking", through one of the people I met in the party scene I ended up doing some modeling to make some extra money. Pretty low rent stuff, nothing glamorous, but a couple hundred bucks a week.

This quickly evolved into the opportunity to do some "videos". It started with just masturbation videos of me lying in bed, or on a couch or in the shower jerking off. I figured I was going to do it anyway so why not get paid for it and I was getting paid $100-200 per day that I did a shoot. I could sometimes do 3 or 4 scenes in a day. The guy running the operation said he was impressed by my "re-load" ability and also that I had just the right cock for it...I'm about 8 inches, decently thick and my dick looks perfectly formed from shaft to head and can blow pretty big loads even after only a little break in between. I knew that these were primarily for gay guys to watch but I didn't care. If someone gets off from seeing me, so fucking what. I did these for a while and then he asked one day if I'd want to do some full sex movies and photo shoots and showed me some of his portfolio and all things considered the chicks looked pretty hot and we were now talking more like $300-500 per day so I jumped right at the chance.

It was a crazy scene and pretty much everything you wanted was at your fingertips. Women and drugs galore. Parties every night after shooting. We were all in the 18-22 age bracket so it was just a no responsibility show. But as quickly as I made money it went back out the door on drugs and partying. Then one night when we were partying at the main house this director used for shooting videos, him and a couple of the other "big wigs" in their operation asked me if I would be willing to do some more hardcore shit. At first I was thinking they meant bondage, s&m type stuff, but they quickly made it clear they were talking gay action. I immediately said not a chance, I was straight and no way I could do it. They pushed the matter (and a coffee table with a big pile of blow on it) and said that all the actors in their gay shoots are straight guys because that is the look they wanted in their videos, strong masculine men, not femboys. The guys just do "gay for pay" and they also said I could make up to a $1000 per shoot depending on the circumstances. At that point my eyes lit up and I think they knew they had me. I asked them more questions and they said I could be strictly a top and receive blow jobs, that I didn't have to get fucked or suck or kiss anyone if I didn't want to. I could also do bi scenes where a female actress or two would be involved. I said, what the fuck, let's give it a try.

The next week they had scheduled me in for my first scene. I was shaking like a leaf prior to which was totally not like me. In the other stuff I had already done I was totally calm and had no issues getting naked, getting hard and fucking in front of other people. It was a one on one scene with me and another guy. I was going to be swimming naked in the pool and then get out and immediately go to the lounge chair next to the pool when the "pool guy" was going to show up to service the pool and eventually me who was masturbating while watching him clean the pool. I actually was having a difficult time getting hard which was totally not the norm for me, but he came over and began blowing me for a while and soon enough I did get fully hard. I had sunglasses on and just kept my eyes closed and picturing hot women. I put on a condom and ended up fucking him in a few different positions and then to my surprise he end up blowing his load on my chest as he was riding me, then slid off my cock, dropped back down and sucked me to completion taking my load all over his face.

I said afterward that it wasn't that bad, but I didn't think I wanted to do it again...until I got my next offer and more cash. It went on like this for a while and me just doing the fucking and getting sucked. I still was primarily doing straight shoots though. Then the director came to me with a proposal for a scene. It would be me and this girl I had done some straight scenes with and we would be a "married" couple and then another guy who was coming to our house to do some repairs. But he wanted it to be a scene where me and her completely serviced this guy. We all were going to suck and fuck each other, no holds barred type stuff. I was extremely hesitant but he offered up my biggest payday yet and it was a good chunk of money for 4-5 hours of total "work". I was so far gone into the scene at that time that I agreed and said let's do this.

The day came and again I was nervous. I did all my usual prep on my "manscaping" and where I normally do everything I can to keep myself fresh down below, this time I added the step of the diet one of the other male actors recommended and his full enema routine to completely clean me out. The worst thing on a porn set when anal is involved is having a shit accident. It came time for the scene and we were in the bedroom on a king size bed where I was fucking the girl for a while then the "repair" man came in, he joined in with me "thinking" he was just going to play jointly with my wife but then he starts licking my balls and ass and pulling out my cock from the wife's pussy and sucking on it. We go through some more motions and she is sucking him then she tells me she wants to see me suck him and this is it, the moment I took a cock in my mouth. I did what I had to do and then after he fucks her it was my turn to take his cock. I was laying on my back as she sat on my face and then he started fucking my ass. Hurt like hell but I had to put up a good front. He even made a comment that got into the video about how tight my ass was. Anyway, we finished the scene after everyone had been fucked and sucked and I went out that night with some of the other people from set and we got destroyed on drugs and booze. I was fucked up beyond belief and when I got home that night I said that was it, I was done. Absolutely no more of all of it. The drugs the porn, nothing. The next day I called up the director and said to pull me from the stuff he had me scheduled for the next week. He tried to convince me and told me what a fucking amazing job I had done the day before, but I told him I had to get out. I couldn't handle the life and really was regretting all of it. I pulled the plug that day and never looked back.

So, somehow through all of this I didn't flunk out of school. I ended up completing my degree and living out a pretty mundane, boring college life and working a bullshit part-time job in one of the offices on campus answering phones and shit. Really nobody in my "normal" life had any clue about what I had done. My parents were none the wiser about anything I did partying or whatever and were proud as could be the day they saw me get my degree. I started a job with a top consulting firm and in the decade plus since, have worked hard and progressed so much in my career that I look at the "crazy" money I was making from porn and laugh at how little it is compared to now. I am engaged to a very attractive and smart girl who is an attorney and makes plenty of money herself, but also has no clue about my prior life.

I guess my biggest fear is that one day I am going to come on here and see one of my videos front and center. I know they are out there in various places on the web, but they obviously weren't under my real name and the look I had back then was very different than it is now where I am clean cut hair, have a beard, and even back then in a bunch of the scenes I had bleached blonde hair for a while and a deep Floridian tan. I guess my real name and SSN is on file with the porn company somewhere so that could somehow get out, but generally speaking I got away free and clear without any repercussions. Crazy the journey our lives take.

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...

This weekend was crazy, my sister in law and he husband were over for a BBQ. So as the night went on we decided to play truth or dare. The game started slow and boring , so decided to bring out a joint. So as we took shots and smoked the joint , I decided to step it up a notch. I asked my brother in law if he ever fantasised about hooking up with my wife which is his wife's older sister. Everyone got quite at first and his wife asked" so have you fantasised fucking my sis?" He got an red and answered yes. As my wife passed her sister the joint she asked me if i ever thought about fucking her. I almost spit out my whiskey. My wife asked "so have you?" I answered with out hesitation " fuck yeah, maybe every other day," she immediately replied" I been wanting to fuck you too." My wife took a hit and asked her sister truth or dare. She took dare and for some reason my cock got hard. My wife said" I dare you to kiss my husband" her sister looked at her husband and he said ' don't look at me, you took dare."she slowly turned around and asked her older sister." Are you sure about this" my wife replied " yes as long a we all promise to keep this a secret." We all agreed then my brother in law, stoned as fuck asked" so does this mean we are going to swap our chicks? " I looked at my wife and she answered him ," yes ,I know you always look at my tits when we are together." She agreed if we were all good with it. Everyone agreed and so it began. Her sister sat next to me and giggles. She said" I always been wanting to do this and know I'm nervous. So I dim the lights and light up the candles. As I sit down she says" Fuck it" she leans over and we begin to make out in front her
husband and sister. I open my eyes and see my wife kissing her sisters husband. We move the party to our bedroom. We are laying next to each other and our wives begin to suck our Dicks. It was so hot watching my wife get fucked while her sister is ridding my cock. We fucked all night. My brother in law passed out first, he never drinks or smokes. My wife sister crawled next to me and my wife and asked me if I would fuck her and her sister at the save time. I never cummed so much in my life. We schedule another fuck fest next weekend in vegas. We are sharing a room😉. I only have a couple ofpics, for the vegas trip I will record it. My wife is the dark haired one.

i confess, i really want a girl to fuck my ass with a stapon, or a tranny to fuck me, i've used dildos, and vibrators and love things being in my ass but im not attracted to men. and i just want a real chick with a dick or a girl to strap one on and fuck me until i cant sit down without being in pain.

For many years I jerked to pictures and videos of traps. One day I took a trip and had an experience for myself. The fantasy was way better than the reality.

The trap looks good when they are all done up and you are in the right light, but when you get back to the hotel most of the shit comes off. The sexy legs and height fall when the shoes come off. The tits fade away when they take off the bra. Most of the real traps you encounter don't have the money for real fakes. So they just use push-up bras to make it look like they have tits..

Both of you normally want a shower before you get to the dirty, so when the makeup eventually comes off you are left with a petite fem dude with girly hair. Once you get down to business it also kinda sucks. You only have two holes to fuck with. Get some head is fine, then its all downhill.

Playing with the d is kinda fucked up. You aren't playing with the d of some hot passable fem shemale like you see in pornos. you are playing with a dudes dick. Its like jerkin yourself off but without any feeling. Blowing is another story. With a condom on its pretty much like sucking on a balloon, and condom off is pretty gay haha. No but you have to be careful with STDs and shit. Who really wants some strange dude blowing loading in your mouth.

I guess you could ask them to stay dressed, but I know my balls stink after walking around all night, so I can only assume theirs do too?

Not to mention the level of crazy you have to deal with with a trap. They may have an STD. They may try and rob you. They may try coming back unannounced to your hotel. They may beg for money. I've had all but the STD thing happen so far.

Chicks are way better. They don't look quite as good without all the shit on their face, but it is pure woman. You wake up in the middle of the night next to a chick you feel pretty good. You wake up next to a trap you met on a drunken night out and the only think you think is how can I get her the fuck out of here.

Am I the only one that think JOI (jerk off instruction) is the most boring shit ever.

Even ones with incredibly hot chicks don't even make my dick wiggle.

My buddy calls me up one time and  asked what I was up to I told him I was just chilling what's up with you ? Hes like you remember so and so I been friends with forever. I said yeah the tomboyish chick she's with that one guy . He laughs and was like well her and him got into a fight and long story short hes not gunna be back for awhile , so I told her she needed some rest and gave her a few pills to help her sleep.  She's out cold just to test to make sure I put my cock in her ass and cummed on her face . You should come over and  get high and fuck her with me . So that I did I got there and walked in to see her sound asleep and he was facefucking her . So I went over and whipped out my cock and put it in her pussy omg she was so tight and it was so arousing knowing she was dreaming n wouldn't ever remember or know . I asked him if hes been cumming in her and he said yeah like 4 times already . He said you about to go I said ya so he barried his cock in her throat one more time and said once you nutt I'll nutt in her two just make sure you go in deep so it doesn't come out right away so I prompted her up so I could go as far as I could and exploded I think that was the most I ever cummed I could feel her pussy about to over flow so I pulled out and he stuck his cock in as far as he could pushing out my cum a little and he cummed  when he pulled out her pussy was over flowing with cum then we used her mouth to clean the cum off our dicks and balls we spent the whole night getting high and using her . A few days later her bf came home ig wonder what he thought after feeling she was lucy ..... lol anyone have any similar experiences or anything like that ??? 

Friday Night….

On a warm Friday evening back in 2019, around 6p, I get a desperate call from my best friend… “Can you stay at the house this weekend, entertain her, please” he desperately begins the call with? “Her” is his wife… I chime in “yeah man, she’s definitely feeling lonely lately” I say as I push for specifics…

(her and I chat, he and I chat, offering my opinion is very common as this has been the topic of conversation for quite some time)

Ignoring me completely, he continues,

“She keeps busting my balls, calling every 10 mins. She feels isolated, alone, you know how she is!” Again, I chime in, “brother she’s 40, the kids are almost out of the house, she wants you to spend time with her, take her to dinner, do shit”. He wants to respond but has nothing, he knows I’m right. “Brother, you both can afford to go do things, she wants to go places, experience life”.

For the record, and totally off topic. this man’s wife has the greatest pair of big fat tits. For those who think “bigger is better”, this is the one! Furthermore,
she’s thick but tone with dirty blonde hair, about 5’7”. Thinking about it, she has Kitty Lee’s body with a much prettier face.. A very attractive woman with a body built for fucking.

(according to hubby, she has a high sex drive and is very open minded… Cocksucker hit the lotto for sure)

With a long sigh he annoyingly utters what I could see coming from a mile away, “I don’t have time for this, Bobby is about to go on, can you stay at my place and keep her off my back so I can enjoy myself?”

And there it is…..

Honestly, he’s frustrated, I get it. He plans ahead for this weekend long festival well in advance, keeps her in the loop through the entire process, it’s kind of fucked thats she’s laying this guilt trip on him while he’s hours away. I’m torn, he’s been dropping the ball with regard to their marriage for a while now.. Then again, this is his once a year “get fucked up and jam out with thousands of dirty hippies weekend, “I suppose she should honor that.

Regardless…

Reluctantly, I respond with Sure man, I’ll head up there now and hang with her….” (honestly, I just want to hang at home, rub one out and crash, it’s been a long week but fuck it, she’s good people and fun to drink with)

Relieved, he replies “text me when you get up there, I’ll call and let her know, thanks brother” and quickly hangs up.. I set the phone down, take a deep breath, collect my shit and prepare for my hour long trip….

A bit of background on the friendship. Buddy and his wife married young, 18-19, had kids, they’re in their teens. We’ve known each other for about 20 years and they are 4-5 years my senior.

For the last few years we do dinner on Friday evenings at their place, a modest spot in the middle of cow country. We smoke, drink and eat well. I normally stay the night, sometimes sticking around on Saturdays to help with ongoing renovation projects.

We’re all an open book by the way, we know everything about each other. It’s actually very nice, I enjoy their company, as they definitely enjoy mine..

I’m divorced, have a great job and a high school age kid. I also have a very comfortable couch and plenty of food in a decent suburban apartment.
An apartment I will enjoy some other time, my drive is complete..

Teresa (wife) is on the porch, shorts, tank top, drinking a rum and coke. She has her hair in a ponytail, which is new for her. She normally dresses like a Sunday school teacher. Her hair always down, outfits very conservative, “boring” is the best way to put it. She certainly doesn’t show off her figure, her gigantic tits always put away, which is a shame quite frankly..

With a hug and peck on the cheek, I make a sarcastic comment, as I normally do, “sweet handle bar, you’re missing one side”. Teresa gives me a “you’re not funny” smirk” and proceeds to tell me that she’s been “experimenting with new styles”.

I waste no time, “you got it, flaunt it, I know Sam (hubby) would like to see more of you experimenting”. She immediately lets out a laugh, like, a quick chuckle filled with doubt, if that makes sense?

Again, in a serious tone I proclaim, “seriously, switch it up, show him you still got it, let him see other men gawk at you, get that little head going…..” She looks at me defeated and says “he knows what I have, what he has access to. He chooses to ignore me” using her hands to outline her breasts and body, exactly how the Price is Right women would display a new prize.. “I’m lonely, tired of being treated like I don’t exist. Months ago I asked him to sit the festival out” she exclaimed. “I asked if we could go away, focus on us for a minute, that I needed him…” Starting to well up, she rhetorically asks “Where is he” as she walks into the house….

So here I am, barely been there 10 minutes, she’s already crying and I’m on the porch by myself thinking “you couldn’t of talked about something else, you had to immediately bring up her failing marriage, good job jackass”….

She’s a strong woman, emotional and poetic, but tough. It wasn’t long before I hear her calling my name from inside the house. I take a deep breath and head inside. Teresa is in the kitchen, she cleaned herself up and is mixing both of a strong cocktail. Without missing a beat, she hands me my drink, we cheers and take a sip as she immediately picks up from where we left off.

As she starts to speak I take a step forward and gently lean in to give her a warm, comforting hug. I definitely surprised the shit out of her. At first she was stiff as board, cold, surprised at my very forward act. It took a minute before you could feel her body relax…. Not saying a word, we stood there hugging, my arms around her upper shoulders, hers around d my waste. Both of us, a firm yet gentle embrace, you could tell it meant something. It was quite nice if I’m being honest.

(being a dude, I have to point out how great her tits felt pressed against my chest, I finally have visual confirmation, as well as touch, of just how fucking big they are. Her puffy hard nipples, pressed against my chest, perfecto!)

After what felt like 20 minutes, I now have a rock hard dick so I pull away. “You’re a smart, beautiful, sexy woman who deserves happiness” I say, as I try to conceal my very obvious excitement. She looks at me and smiles as I conclude my thought “ponytail and tank top, my new favorite look” as I look down, laser focused on her giant titties that were currently on display, hours and hours of fun, beautiful cleavage, no bra)

Remember when I said “we know everything about each other?” It’s no secret hubby and I both have a thing for huge giant titties, conversations she’s been privy too, normally just giggling and walking away.. Staring down at them was certainly knew, however, she was well aware of my infatuation, in general, for big natural breasts. Yeah, I’ve looked at her, but nothing more than looking, in my head she’s a no-go, off limits..

It’s at that moment, still in our embrace, she says “I have to come clean”. Oh boy” spews out of my mouth as I question her, not with words, but wi5 the look in my eyes….

“I’ve had a crush on you for the last 20 years.” And don’t worry, Sam knows, he thinks it’s funny. “But, I want you to know, I’ve always had a thing for you.” Shocked, I ask “When me and the ex visited you, is this why you treated her poorly? Shaking her head in agreement, Teresa responds “that bitch took you for granted, treated you like shit for years”, you deserved better, fuck her”.

I laugh out loud as I share “she’s my one and only bad lay, dead inside and in the sack, terribly boring with no enthusiasm, a waste……” Teresa chuckles and shares “well, at least Sam has a big dick but I fantasize about other people when he fucks me. The one or two times a month he does fuck me, I keep my eyes closed, I go through the motions to keep my life semi-normal, but I’m not in love with him anymore, too many years have gone by, I’m over it”.

“Teresa, I had no idea it was this bad, I know he can be a dick, but never thought it was on this level, what are you going to do?” Teresa takes a step back, grabs our drinks and confidently shares “Hanna has three years of school left” as she hands me my drink, “once she graduates and goes to college, I’m leaving”. Her eyes start to fill with tears as we both take a big gulp of intoxicatingly strong rum and cokes… She leans over, grabs a tissue and wipes her eyes as we both take a well deserved gulp of mind numbing spirits…

Our drinks polished off, Teresa quickly time for another” as she grabs my glass and heads for the counter…… Unsure of what to say, completely blown away with the last hour of my life, Teresa swings her head around, ponytail in the air, and says “I’m sorry if my confession has made you uncomfortable, that was not my intention, I just needed you to know” as she turned her head forward to focus on drinks.

I don’t know what came over me, but I felt this urge to hold her.. The last hour had quickly turned in an emotional adventure for the two of us. However, she had a minimum of three years of hell to go through, which saddened me. I had lived that life and it miserable, my heart ached for her.

Throwing caution to the wind, I walked over and wrapped my arms around her stomach, careful to stay below her breasts, resting my head on her shoulder. She took a deep breath and reached for my arms. I whispered in her ear, “I’m here for you” as she let out a whimper and sigh of relief.

It wasn’t long before my dick was coming to life.. She was absolutely pressing her ass just enough for my guy to feel it. Moving from side to side, T was knowingly trying to get me hard and I could care less. I whisper in her ear “I know what you’re doing”, as I begin to mirror her movements, moving my dick from side to side, pushing in….

With both a whimper and deep breath Teresa takes her hand and begins to run it along my covered dick.. “Oh yeah” she says as I let out a gentle moan, immediately, and slowly, moving my fingers to the base of her giant breasts. I think to myself, “Finally” as I open my hands and grab the biggest pair of tits I’ve ever felt. Teresa let’s out a soft moan, catching her breath enough to say “please fuck me!”

Im so fucking hard I can’t stand it, as I respond “soon baby, soon” as I move my right hand inside her waistband, her pussy and clit my targets. She moans out again as I take my left hand, already squeezing and pinching her left nipple, I quickly grab her throat, pulling her head to my my face, forcefully, T whimpering away “How bad do do you want my dick in you” I whisper as she runs her tongue along her upper lip..

3 seconds later, and not missing a beat, Teresa, her hand in my pants now, my dick in hand……. Actually, it’s more like, “Teresa the magician, her hands suddenly down my pants, with a king fu grip on my dick, a grip so tight she could tell you how many beats per minute my heart was pumping” she’s rapid fire jerking me, it’s to tip, long strong stokes……

In return, my left hand still gripping her neck and my right hand buried in her pussy, I have two fingers fucking her pussy while rubbing and pressing her clit with her thumb.. T, well, she starts to moan and loudly and shake as she nutted all all over my fingers….

Teresa hadn’t been touched like this for some time, that was evident!

I nibble on her ear lobe, as she catches her breath, still feeling the effects of my fingers…. I whisper, “now you can have my dick”, slide me into your pussy” as I turn her to the right, and bend her over her kitchen table.. With my dick rock hard and still in her hand, I grab her ponytail and make my way for her opening.. With my left hand, now gripping the sexiest tits I’ve ever played with, I turn her head toward mine and say “that’s my pussy” as she loudly grunts out “take your pussy” as she rests my dickhead at the opening of her love canal..

Deep breath, deep breath as I tease Teresa with my dick, ready to push in fully, sliding in, the phone rang.. I pause, caught of guard by the phone, I say “fucking figures” as T slams her ass backwards and takes my dick…. “Yeah it does” she says as I quickly remember what my objective is….Pony-tail pulled back, left hand firmly holding a giant tit, sexy mom/wife panting as her wet pussy is ready to make a mess, I lay into to her, hard, deep, and aggressive, phone ringing off the hook…..

Let’s be honest… This didn’t last long… 5-6 minutes later, as our hearts race, Teresa screams out “you’re going to make me cum” in what I can only describe as a surprised tone.. “You’re pussy s soaked i murmur, ponytail still in hand, her back still arched, her moans and pants, now similar to a countdown. She’s ready to blow boys!! I give her everything I have, table creaking, both of us moaning loudly, Teresa’s pussy tightens…..

That’s all it took! In unison, I thrusted as deep as I could into her tightened pussy, and fucking unloaded as T let me know just how appreciative she was, nearly falling over as she came all over my dick. With her ponytail still in hand, left titty still firmly in my clutch, I bit on her ear and neck as we both appreciated just felt the effects of a fantastic nut……

A few minutes later, both of us, chuckling and giddy, completely spun from what just happened, get a drink of water. As I’m guzzling like a thirsty African baby, T pipes up and says “I haven’t came like that in years” as she stood back and took a sip of water, almost shocked at what happened. I ask if everything is ok and she quickly says “oh yes” as she intentionally spills water out of her mouth and down her huge jugs. “Thirsty” she asks as I quickly do what a man with a huge natural tit fetish does, as I grab both tits, in a loving embrace, pull them to my face, kiss her deeply and begin sucking her nipples………

Oh yeah, the ringing phone? That was Sam, I forgot to let him know I had arrived… No worries, 60 seconds after pumping his wife full of my nut, as I’m sucking her tits, Sam called back.. T answered, out of breath, Sam completely unfazed, he babbled away, praising me up and down to T, as she stroked my dick.

Sam, “so happy” that I “gave up my weekend to help him out”, requested me on the phone.. “Yo brother” I shout as he immediately thanks me then starts a long winded diatribe, excited to share the highlights of the bands, the setting and the great food. T, left to her own devices, grabs my dick, fat tits swinging, full naked body, she leads me by my dick to the couch as she holds up two fingers…. Sam, he’s still raving about his stress free hippy induced weekend, clueless to the fact that as I say ”sounds like so much fun brother” his wife is on her back, legs spread, pussy soaked, guiding my dick back in the very same spot Sam used to call home.. Round 2 has indeed started,,

Sam called back the next day, he and I on the phone for quite awhile. I remember him saying “its much more relaxed now” as he immediately started the process of repeating the same shit he said the night before, which led to him thanking me again for getting his wife off his back… “Yeah man, she seems happy to have company” I blurt out as he asks for me to put her on the phone…

“Oh man, she’s at the market” I say, as Sam chuckles quite loudly, blurting out “yeah she loves spending my money,” as he chuckled on, eventually saying “I’ll call later” as he hung up…. I’d imagine he saw a half naked dirty chick, or dudes eating shrooms, which is why he just hung up.. He was “on to the next one” ass they say…

Speaking of which…

I’m triple checking to make sure the phone is off screaming out “I can’t hold it anymore!” T, mouth soaked with saliva and spit, and clearly not at the market, grabs my nuts and slams her face to the base of my dick, not missing a beat, or drop, as she emptied my sack deep in her throat… Like a bitch, I screamed out as I felt every last drop empty my nuts. By the way, a second orgasm not long after a man’s first orgasm is quite intense, it’s quite nice!

Teresa enjoyed sucking my dick with her husband on the phone. Admittedly, I enjoyed it as well. The threat of getting caught is quite addictive. So much so, we test the limits of our sexual prowess weekly. I fuck my friends wife regularly, right under his nose..

Case in point-

Friday before Christmas, while Sam sits in his recliner, stoned out of his mind, eating cookies zoned out, Teresa and I will go for a night walk. Sam completely unfazed and happy to have the tv to himself, clueless that his wife and over night guest are 20 ft away, watching him watch tv, fucking like school kids. Me squeezing her nipples, smacking that ass, pulling her hair, drilling her pussy! Teresa, holding onto a tree, taking my dick from behind like the good girl she is, her fat little pussy tightening as she cums, while empty my seed deep into her, fully embraced, while hubby watches cartoons or some shit…

Or right now.. He just got in the shower. T, in a flannel, no bra, immediately goes in and grabs a tissue, making sure the coast is clear. Sam, fully engulfed in washing his ass has no idea his wife literally walked out of the bathroom, about 10ft, slide her pants down and sat on his buddies dick. Of course, I’m unbuttoning and pulling the monsters out, as the smell of Irish Spring permeates the air..

Till next time..

I spent the weekend with my cousin-in-law. I'm married in, but we've always been close. And I've always found her insanely attractive. Not just her body, even though that is amazing as well. She was a college athlete and still finds time to workout. She's got those firm, tight legs that always look good in those short-shorts. The ass she has matches that. Thank god she always puts them into shorts or tight yoga pants. She isn't carrying much in the way of boobs (as often most athletes aren't), but she makes up for it with a tight tummy and a body where nothing sags.

Sorry, I got off on the point of what makes her awesome. It's hard to do when thinking about her. She's a down to earth chick. Loves beer, football, and relaxing. She doesn't do many things that a lot of girls her age enjoys. The 24-27 age range.

She's always given special attention to me. Always finds me, seeks me out, asks me to hang out and always wants to hang out when I call her. Seems pretty obvious, right? We've gotten drunk multiple times together and I've always taken care of her, cuddled, shared a bed, etc. We've never done anything more than that.

The jist, I really think she wants to but she was raised super conservative catholic. Her parents literally tripped when she got a tattoo (and has given me grief on my tats as well) and damn near disowned her.

This weekend, she invited we were alone. No friends, no family, just alone. I wasn't expecting this and actually thought friends/roommates would be there. We drank quite a few beers, watched football, and a few movies that I force her to watch. I'm just over 30, so I feel I've got a good grasp on movies she missed out on when younger.

We talked about marriage, boyfriends, and sex. Nothing got awkward, we just talk like best friends. It's amazing how easy it flows when talking to the right person. Next thing I know, I'm talking her into a back massage. I'm pretty good at this and next thing I know, she's leaning back into my arms. We keep talking, I'm working her hands, arms, and neck. She then decides it's time to go to the bathroom.

When she comes back, I try to continue the massage and she said that she couldn't do that to me. It's unfair to massage her all through the movie we were watching. I told her it was unfair to let me stop doing what I was enjoy doing. She resisted a little verbally, but finally slid back between my arms. As I kept working her back, once again she leaned more and more into me. Before long she was entirely leaned back with her head on my shoulder. I kept massaging her arms, neck, scalp, and before long the top of her chest. I asked her if it felt good, she smiled and said, "Yea, I never knew you could get sore there."

This went on for another 20 minutes. At the end of the movie, she got up slowly and we went upstairs. I wanted nothing else but to lay in that bed and hold her. Well, maybe I did want more, but that alone would have made me happy. We laughed, wrestled for awhile, I threw her on the bed, and she told me I should go to sleep. She got up slowly, not listening to my pleading about staying in her own bed, and mentioned sleeping in the guest bed while I had her bed.

I relented, knowing I already had crossed a line that could have gotten me in trouble. Besides, we were both pretty hammered and I didn't want to force anything. I laid their in her bed, listening to her shower and change for bed, wishing I could see her body. She comes in, throws her clothes into the hamper, says goodnight, and hurries off to bed. I laid their, visions dancing behind my eyes, wishing that movie was another 3 hours longer.

A thought finally popped into my head. I went over to her hamper and dug through her clothes, pulling all the panties I could find out. Man, for a catholic girl, she had some sexy ass panties. It was a shame no one saw her in them every night. I finally found the ones she had been wearing, a sexy sheer black lace cheeky shorts. I sniffed them, and realized that she had been very wet. I made my haul of undies back to her bed and found another sexy, soft lace one to wrap around my dick. I piled the undies all around me and jerked off until I came into at least 3 of her panties.

It seemed like a shame to leave them, so I selected a g-string I thought wouldn't be missed, pocketed them, and tried to place the undies back into the hamper without too much obviousness. I laid back down, and fell asleep while smiling about those undies.

The following morning, we get up, make and eat breakfast, then spending the morning discussing the football games, the week to come, and how we were getting so old that we can't drink like we used to. I casually brought up the massage and how she'd owe me one next time. She laughed and said she would, but don't expect much since she's not good. I didn't know how to tell her that my mind was on her massaging my cock, but I'm sure the growth in my pants was trying to send signals. It turned me on even more knowing they were pressing against her panties in my pocket.

After a little bit more gossip, it was time for me to go. I loaded up to get back on the road. She came out in the tightest yoga pants I had ever seen. There was no way she was wearing panties this morning! She gave me a huge hug and said she had fun. We said goodbyes and I was off. Later down the road, her and I shoot a few texts back and forth about doing this again real soon. She thanked me for stopping by and how much of a blast this was and asked me to come back real soon.

Now I jerk off to her panties almost every chance I get. I love my wife. She's special, unique, and beautiful in her own way, but there's just something about the casualness of being with her cousin that drives me wild. I'm sure if her cousin and I were single, we'd have been dating by now, but I'm ok with us just being friends and never getting to that state. Honestly, I think I enjoy the closeness we have without worrying about relationships, wedding bands, and family.

I would like to move this to the next level. It wouldn't have to be sex, but helping each other out when we are needing some release seems like a very friendly thing to do! And how everything just stays normal, even after our "massage" got a little close. The thought drives me wild and it is probably the one thing I'll never be able to talk to her about...