My wife is going out of town at the end of next month and I want to try and get fucked by another guy. The thought turns me on so much. I’ve sucked a few dicks in the past but never tried anal. Any tips or pointers? Yes he used dildos and other anal toys but they just aren’t enough. I want to just bend over and get railed by a regular sized cock. Nothing too big. I don’t consider myself gay because im not emotionally attracted to men. Im only physically attracted to cock and cum. Has any one else been wanting to try it for many years and then finally got to do it? Maybe we can chat. 

I've just turned 50 and with that age bracket - there comes problems, the main ones being an enlarged prostate and erectile disfunction. I've got some Cialis and sometimes I wonder if a lot of the ED isn't psychological. My wife and I have been in an open marriage for a few years, she's bisexual and I love the fringe benefits of it. One night she went to a bar and brought back a very attractive female, who was about 45 years old (same age as my wife).
They were both tipsy, and my wife introduced me to Jessie, raven haired, medium sized tits and a nice tight body. They sat down on the couch and invited me over. Small chit chat ensued. My wife poured her some wine, and she drank some too - I refused because I knew that just in case I was going to get lucky, drinking wine would screw with my ED. I stepped away for a minute and went into the bedroom and took a Cialis, got a drink of water and chugged it. I went back into the living room where they were sitting and they were making out. Jessie noticed me, and stopped kissing my wife.
"Oh, I'm sorry I thought you were going into the other room to give us privacy..."
My heart sunk, looks like I wasn't going to be sticking my dick into Jessie tonight.
"My bad," I said, looking down - defeated.
My wife saw that I was a bit hurt and explained, "Jessie is a lesbian, she isn't into men... she doesn't mean any disrespect..."
I should really give them their privacy, I thought...
"Ok, cool - I'm going out."
So I got in my car and drove around, no destination - but then I thought about it, I just took a Cialis. Pretty soon my cock would be begging for some wet hole to fuck. I guess I could get sloppy seconds once my wife is done with Jessie... but that could be a while, so I decided to go to an adult bookstore a few miles from my house. Weird shit popped into my mind, "Maybe there's a hot chick I could fuck in a glory hole, I've never done that... or maybe I can get an escort or hooker..."
All kinds of shit was going through my mind. This bookstore is a 24 hour store, so I went in and it was busy as fuck. All I wanted to do was ask the guy behind the counter where to find a lady of the evening, but too many people were around him. I noticed two women looking at toys and giggling, the looked like they were in their mid 20s, so I tried to blend in and started looking at masturbators. The small version of the Fleshlight was 79$?! I was taken aback and shaking my head. I was trying to maintain the "no eye contact" creed while I browsed all kinds of toys. I stopped in front of the 'prostate massager' section, all shapes and sizes - I never had a massager or anything anal but I heard of the wonders of prostate massages. Too bad my wife and her new friend were fucking around or I'd definitely try to experience something like that. I heard a little whisper behind me, something like "you ask him..."
I turned around and it was the giggling ladies. One was a brunette with very dark brown eyes, the other woman had purple and white streaks in her hair, but had cool blue eyes. Both were very attractive.
"Hmm? What's up ladies? I asked.
They blushed, "ummm, are you gay? No offense if you are... we're just wondering about the prostate massagers..."
I blushed, "OH, NO NO! I'm not gay, I'm straight..." so I did something that I never did with a stranger, I opened up, "I have ED, and I've done some reading and some people say these things help. I just turned 50 a few days ago, and my wife is at home banging her girlfriend and I'm just here... browsing because - well I just took a damn Cialis and ... well that's that. Sorry if it's too much information... I'm not a creep or anything."
The brunette smirked, "You don't look 50 at all, I thought you were about 35 or 40 at most."
Purple haired girl nudged her friend, "he's cute for a 50 year old..."
They both giggled and blushed. I didn't know what to say, this was odd because I've never talked to anyone in any adult bookstore given the exception of the checkout clerk. They saw I was struggling too, and the purple haired one spoke up.
"So you let your wife bang other women? That's kinda hot... I just broke up with my boyfriend, and Amanda just doesn't like dating at all so we're both kinda of single but we keep each other company if you know what I mean?"
My dick twitched.
"I'm Mike," I said, extending a hand out to the purple haired girl. She took it, and replied, "I'm Mary and this is Amanda, nice to meet you Mike."
Amanda's face was turning a bit red, "Mike, since you don't have anything else to do, you want to join us for some coffee? There is a cafe just down the street!"
I agreed, and started walking towards the door when Mary said, "Mike, aren't you forgetting something?" while pointing to the prostate massager.
I picked up the smaller one, $45... and headed for the check out. I paid for it and the clerk put it in a black bag. I turned around and Amanda and Mary were gone. Well there goes that. I left the store and walked to my car.
"Mike!" I heard a call from a distance, it was Amanda waving from across the parking lot.
"Oh I thought you both bugged out," I laughed.
She took me by the arm, "oh hell no, and miss the chance to hang out with a sexy 50 year old with ED??"
We both laughed. Mary, Amanda and me walked down the street arm in arm to a cafe. We sat down and talked for what seemed to be hours. These two women were not only attractive, but smart as hell too. I asked how old they were.
Amanda spoke first, "I'm 23, just turned 23 in January."
"I'm 26," Mary said sipping her coffee.
I laughed, "you're both half my age!"
"Older men are sexy, our generation likes older men. You guys know what you want and you're not complete idiots, or assholes," Amanda said.
Again, my dick twitched.
Mary looked me in the eyes, "we're freaks in the sheets, Mike."
I couldn't help myself, "is that an invitation?"
Amanda put her hand on my knee, "why would two girls in their 20's be hanging out at a bookstore at night unless they had an agenda? You were the first decent guy that came in there and we were in there for a while..."
My heart started racing.
"We're gonna put your little toy to the test, if you let us..."
I was in for an adventure of a lifetime.
We went back and got in my car, I drove them to Mary's apartment, and we all went inside. There really wasn't any wasting time. They stripped me down as soon as the door was shut. My cock was in Amanda's mouth as Mary's tongue probed my throat. My hands wandered from Mary's sexy tits, down to her dripping wet pussy. My cock was rock hard as Amanda shoved it all the way in her mouth to the hilt. I'll admit, I don't have a huge cock, I'm just normal - but the way she was sucking my dick put me on top of the world. They led me to the bedroom and Amanda pushed me down on the bed. Mary unwrapped the prostate massager and started playing with it using her pussy. She let it slip inside her.
I got kind of worried, I never had anything going up my ass before... so my erection started going down.
"Oh, baby - nothing to worry about - just relax..." Mary said.
Amanda climbed on top of my face and I started licking her pussy, she smelled really good, and her pussy tasted sweet. Amanda started moaning and I grabbed on to her nice soft ass to steady her.
I felt Mary playing with my cock, pumping it with her hand, then I felt her mouth around it and I was hard again. As Amanda rod my face, Mary mounted my hard dick and I felt how tight she was. I moaned as her pussy stroked me up and down.
Amanda came hard on my face, squirting a little - but I didn't mind at all. I held her against my mouth until she almost passed out.
Amanda crawled off to the side, and shivered. I could see Mary in all of her glory, bouncing on my cock, smiling. Her nails sunk into my chest as she rode me, moaning. Amanda got up and started fingering Mary's clit and licking her tits as she rode me. Soon Mary came hard, and I could feel her warm pussy juices dripping onto my balls.
"Your turn," Amanda said to me as she grabbed the prostate massager and rubbed it on her pussy.
"We gotta get it nice and wet Mr. Mike..."
Mary spit on her fingers and started rubbing my asshole and Amanda slowly pushed the pussy juice soaked massager in. I moaned in pain, that shit hurt...
"It's ok Mike, we're going to go slow..." and they did.
Mary started sucking on my cock as Amanda slowly used the toy on me. I tried my best to relax. I was trying to focus past the pain... it took a while but Amanda started hitting something that felt so good.
"That's it Mike, relax... we're going to drain those balls..." Amanda said, pushing the toy in, and pulling it slightly out. She started going faster, and then faster as Mary moved her mouth up and down on my pulsating cock.
"Give us all that cum babe, come on..."
I had these two young women fucking the shit out of me... and I felt this weird feeling starting to erupt around my entire body, like all of my nerves were electrified (but in a good way). Suddenly my cock erupted as Mary stopped sucking both of them literally started making out as cum exploded on their tongues and faces. They moaned, they licked my cock and more cum sprayed out. Mary deep throated me, then Amanda did. Then they kissed deeply. I was on the verge of passing out.
"Did you like that, Mike?"
"HOLY FUCK LADIES" I gasped.
They both laughed. They took the massager out of me and put it in a bag.
"I'm going to give you my number, I really hope you call me... I wouldn't mind having more adventures with you..."
"Did you think this was a one time deal old man??" Mary joked.
"You can spend the night with us if you want... no strings, just chill and cuddle and sleep..."
Amanda lit a joint and took a small hit, passing it to me. I took a hit, held it in and let it go as I passed the joint to Mary.
"I'd love to spend the night," I said as we all laid in the bed together.
When I woke up in the morning, both of these babes were cuddled into me. I woke them up and told them I had to go home. They both kissed me goodbye, we exchanged information and they promised me that there were a lot more adventures to come.
When I got home, my wife was passed out in bed with Jessie. Both were naked. Jessie had a tit hanging out of the covers, it was a little saggy compared to the ladies I just spent the evening with.
I started cooking some eggs, but couldn't help of thinking of Amanda and Mary.
I have to confess, I think I am falling in love with two women I just met at an adult bookstore... I've never been treated like that in my life, I felt like a king. Not only was everyone sexually satisfied, we all got along great. Maybe I'm just too deep into a fantasy with two young ladies... but honestly I want more of them. Not even concerned with fucking my wife at this point.

So, I have a confession. More of an admission I guess.

I'm not homosexual, maybe I'm bisexual. It's hard to tell, because I've never been with a man. I've always loved women, and I'll never stop wanting them. But lately, I've been thinking about experimenting with being a "bottom".

I guess I should start from the beginning here. The last girl I was with, I guess it was a year or so ago, was the love of my life. I had finally found the girl I wanted to marry, to be with until one of us died. I was happy, and she was EXTREMELY adventurous sexually. Our first night together before we were a couple involved a threesome with her friend. It was actually initiated by her friend actually. That's another tale though.

SO, after we started really dating, things clicked quick, and we fell in love. Love isn't something that I throw around without meaning, she's actually the first of any of the girls I was with that I truly felt it for.

Sex was fantastic. We fucked like rabbits, we fucked in public, in my car, just, wherever, whenever. I STILL to this day dream about the sex. Well, while she would be blowing me, she would always massage around with her other hand, and one day, she went low and started pushing her finger against my asshole.

I never really got into the idea of having my ass fondled, but she was the kind of girl who would convince me to jump off of a cliff. I mean, this girl was heavenly, with a mix of the devil. Natural beauty, un-dyed Raven hair, tits that were out of this world, hell I doubt I'll ever do better.

Anyway, so she starts working around it, and I'm not so much in a panic, but just wondering what I should do. Damn if she didn't figure it out for me, a quick deep throat made me release whatever pucker I had as I felt the ecstasy of her pleasuring, and she worked her finger right in.

She looked at me, and just held her finger in as she stroked my cock with her other hand, and smiled. I smiled too, because, I loved her, in my head I was worried that if I enjoyed it, she might think I was weird.

Well, more and more times during sex, she would work her finger in during a blow job right to the point where she started working her finger in and out. I didn't stop her, because she enjoyed it, and honestly I did too now. It was an extra pleasuring to my already fantastic fucking.

I decided to pay her back with some ass play of my own one day, and I turned her on her belly as I massaged her, working down along the hump of her bottom, spreading her cheeks and working my tongue in. She moaned in joy as I tongued her ass and fingered her clit at the same time. I had never eaten a girl's ass before, but if there was a girl to try it on, it was her. I had fun, she was very clean, as am I, so I wasn't worried about anything "gross". Who am I kidding, I freaked out at first, but in the moment, you just go all in. You know it.

Well, the next night, she decided to PAY me back for her pleasure. She told me to lay on my back, because she wanted to give me a massage. I told her it wasn't a big deal, because massages didnt do it for me. They still really dont. I don't find them too erotic unless I get a bj at the end. Which I never did haha.

She playfully tells me to just do it, so I abide. She starts massaging me, and after a few moments, I realize she started working a lotion around my bottom. Now, I've been told that if I posted a picture of my ass, and hid the fact that I was a dude, I could have men jerking off to it. I've often considered doing it as a joke. Then revealing that the ass belonged to good ol' me. Anyway, back to the story..

She starts rubbing lotion on me, and beckons for me to get up on my knees and elbows. She starts to use the lotion to stroke my dick and balls, and it feels fucking fantastic. I'm wondering to myself, "My god, how can it get any more awesome??!!" When all of a sudden, I feel a warm moistness start to tickle around my cheeks. I tensed up when I felt her breath roll over my ass, a little warm air against my bottom.

Suddenly, she begins licking and rolling her lips around my ass hole as she strokes. I tried my best to not cum, but it was probably the best feeling I've ever had in my entire life. I came BUCKETS. I'm pretty sure I applauded her.

So, some time passes, and one day after lunch on a weekend, she tells me she wants to start using toys. Again, I've never used toys. Never really figured much for them, as I have the perfect toy for a girl right between the legs.

I tell her to get whatever she wants, and we'll try them out. So, a few days later a package from Amazon shows up at our door (we lived together for a bit in a nice rental house) and low and behold, she ordered a vibrating dildo.

I joked with her and said I was sad that she didn't think my dick was up to par anymore and she laughed and said that they were the same size, she just wanted to try a few things. So the night the dildo came, I was eager to see what she had in mind.

She asked me if I'd fuck her in her ass. I'd never had anal sex with a girl before. Don't get me wrong, I tried. My ex some time before her flew off the bed in pain because I was too big. And since then, its never really been anything I thought of doing. The vagina and mouth work just as well.

I said hell yeah, and after careful careful careful amounts of effort, we got it in, and the fuck began. At first it was slow, incredibly slow. Almost to the point where I was just wanting to take it out and fuck her normal. But, as she always did, she surprised me. She started fucking speeding up to the point where it was like I was railing away at her like normal. I still was careful, I'd read too many horror stories.

In all this, I'd forgotten about the dildo. The purple, ugly, veiny didlo. The damn thing sat next to her as I fucked her ass sideways.

Now, I've watched a lot of pornos. And they've been the best education a man could ever need. I grabbed the damn thing, I never held one before, so it was like holding another man's penis. Odd. I decided I was going to double penetrate my girlfriend. I slowed down enough to work it in, and with the satisfactory moan from her, I did my best to maintain a rhythm. Eventually, I handed the rains of ol' Veiny to her and it was epic. She came a lot, I came a lot, and it was a fantastic night.

A few nights later, because I was out of town, I came home to her in a sexy little number and the ol Veiny on the bed. I figured we'd be repeating the night we had earlier in the week, and I was excited. The way she could work a dick, damn I hate the guy who she's with now...

So, we set about it, and she gets the lube out and starts applying it all over the dildo. I kind of had an idea what she was up to. I'm not a moron, and I'm horny like 99% of the time. The other percent I'm sleeping. She asks if she can use it on me.

I stared at her for a while wondering if there was a wrong answer here. I didn't know if it'd be like Indiana Jones and The Last Crusade, where I had to "Choose Wisely", or not. I decided, since she and I had been having wild nights, what the hell. We only live once.

Well, haha, it didn't work out. I did not have the anal space for anything like that, and honestly, I was terrified. I could tell she was disappointed, but not completely downtrodden about it. She told me that we'd have to work up to it. I agreed, if only to appease her.

So over the next couple of months, she would use two fingers instead of one, increasing slowly to three, to the point where it almost hurt when she was working her hand in and out.

Well, things didn't work out between us, and we ended up breaking up before ol' Veiny ended up anywhere near my ass. This is where I'm at now, and I can't figure out what's going on in my head.

I've had thoughts about having a dick jammed into my ass, and it subsequently railing it. I mean, not just any dick, a fit, young fellow like myself. Not a beary old dude. I dunno, there's just something about it that turns me on. I dunno if its because I still am drawn back to the passion with my ex, and kind of "finishing" what we set out to do, or what. I mean if that was the case, I'd just stick a dildo up there and call it a day. I think there's more to it than that.

I have what some may say is a sexy penis. Its not ugly or funny looking, its just exactly what its supposed to be. And I think thats the kind of penis I'd hope for haha. I see some of them in porn, and its kind of a turn off. So, I know its not the penis that draws me.

I've thought, maybe just a girl with a strap on? But I dunno, I feel like if I were to go that far, why not have it be a real, pulsing, throbbing cock?

These are questions I ask myself all the time. I know I love women, but maybe I'm not opposed to the idea of an attractive man. Only sexually though. I couldn't have a "relationship", per se. I mean, don't get me wrong, I'm a supporter of equal rights, politically, sexually, you name it. I'm just not gay in that way. If at all. I think its a sort of bicurious attraction that I'll never fullfill. I dunno. I just had to get it out I suppose. I don't really talk to anyone about my sexual habits, so I figure a sex message board might be the place to do it.

I confess that I am a man with an addiction to being a cock loving, cum craving, anal sissy slut from time to time. I often dress in my stockings, thong, and little shirt and go into an online chat room to get some attention from, well, anyone. Especially if I haven't had a rendezvous with my "friend" to satisfy my needs in a while. I love chatting about my experiences and sharing online pictures of hot girls, shemales, bisexual pics, and gay men. I also share pictures of myself playing with my cock and ass. When I am in the mood, I share my live stream and when I'm really horny, use a couple of my toys. I like doing this because it really turns me on, especially when guys will let me watch them stroke their cocks too. At the end of the night, my goal is to get so aroused that I have a big load of cum to shoot. I like to cum right into my mouth with either fingers, a dildo, or a butt plug in my ass. I cum so hard but it satisfies my wanting mouth and tight little ass.

I confess to wanting anal stimulation from my fiance. She is super homophobic, so it's going to be a tough sell convincing her it's not about gay or not gay but about pleasure with her. Any tips on approaching somebody so prude to the topic?

also when you've actually done it do you do it like doggy style or how is it best?
I am thinking about getting a toy, any recomendations on type or anything like that?

Just a bit more background we are 22 y/o and have a pretty healthy sex life but i've always been the kinkier one. She does take it up that ass, but the usually is the kinkiest we get.

I have never had feelings for other guys and have never had any problems finding ladies. I am in decent shape, tall, but have always had kind of a bubble butt. Not abnormally huge but enough that I have noticed gay guys checking me out. I have been hit on several times by gay men but as I said, I have no feelings for guys.

Well... After seeing how the M4M section is exploding on craigslist and after seeing several confessions on here about non gay guys experimenting, I have to confess that I did a little experimenting myself.

Seeing as how most women don't like anal I really toyed with the idea that a male ass is the exact same thing... and with the lights out... what's the difference. I also was willing to please the other guy if I had to.. with my ass or hand as I really wasn't into putting a dick in my mouth.

So I put an add up on craigslist explaining exactly what I just said. That I was virgin to guys but was curious.

Here are the pictures I choose:

figured a full body shot with some ass pictures because that's what seems to attract other guys to myself.

I got a ton of replies but most of them just wanted to fuck my ass and said nothing about me fucking them except for one guy.

He came over to my place and we both said our hellos then he asked if I could suck his cock a little. I was hesitant but was uncomfortable with the whole meet up at this point.. so I did.

Yeah.. he was fucking huge and instantly hard as a rock. At this point I was wondering what my kinkiness got me into this time. Sucking him wasn't bad. It did not excite me but I did it thinking I would get my shot at him. He tried to push it all the way down my throat.. but I just could not take it. He was super fucking horny and said he need to get off before I could do him and he asked if he could fuck my ass. Again I hesitated but told him if he went slow and used a condom he could.

You can see how hard he is in this picture. I think this is when I was telling him to go slow. God Damn.. he must have been 10 plus inches and I could tell by the way he looked at me that he wanted to turn my ass inside out. I wasn't really into it.. but its hard to say no in a situation like this.

He gets something from his pants pocket and I assume it was a condom and turn around.

Looking back at the video it turns out it was a bottle of anal lube as you can see here:

This guy knew what he was doing from the start and was interested in one thing only.... Taking this naïve, virgin, white, bubble bottom and leaving a huge load deep inside it.

Another picture that shows how horny he was. He was looking at my ass and that thing was almost vertical.

here he is trying to get it in. I could tell by his shacking he was using all his self control to not just thrust it in and blow a load. Notice the lack of condom and the bottle of lube in his hand.

[IMG]
http://thumbs.motherlessmedia.com/thumbs/46D2674.png[/IMG]

He was slow at first but once he got that first full thrust, he proceeded to just pile drive my ass. It hurt like hell and I really did not enjoy it much.

He then pushed me down on the couch. grabbed my ass, and just punished it with his cock for about 10 minutes. He really enjoyed himself... I can tell you that. At the end he moaned real loud, thrust deep, and blew a huge fucking load.

He climbed off fast and put his pants on. I figured he put the condom in his pocket. He then said he had to go... and I was so nervous I said nothing.

About 5 minutes after he left I felt like I had to go to the bathroom but when I sat on the toilet only cum came out. Its bad enough he did not use a condom... but how the fuck can a person cum so much?

So .. yeah.... I got fucked.. literally. Let that be a warning to you other guys on here contemplating testing the waters.

Fortunately I set up my hidden cam and looking back on it... it is kind of erotic seeing a huge black cock practically rape me, but when it was happening I did not enjoy it..... much.... I think there was a small part of me that liked it as I did not tell him to stop. Maybe it was just the fact that I knew it would make a good video I could watch? who knows.

I still want to try fucking some ass and am even willing to take some cock to do it. Will I ever cross that bridge again.... who knows?

Omegle is awesome! A quick side note: I'm in my late 20's, straight, and an ex gf got me into like prostate play, but I have NO interest in men. If you haven't tried it, you don't know what you're missing. And I don't want to hear anything about gay here. I just don't care. Just like there will be no pictures here.

So just a few nights ago I decided to go on omegle and play with some of my toys. I usually do unmonitored video section and hope a girl pops up. I usually have a bigger dildo out and girls always do a double take when seeing it. Then about two thirds of the girls usually want to see me play with the dildo and get fucked by it. It's fun having a young girl watch and be amazed at it. But eventually it get old with 99% of the others just guys with dicks out. So that's when I start going to the texting section where you can pick topics.

For a while at first I started using the topics bi and lesbian, but I found most girls in the lesbian section have no interest in a guy with toys. That's when I started doing just bi/bisexual topics. The first thing I'd say to every match was "I'm over here playing with my toys (;" and ask for their asl. If it's a guy, on to the next, but if its a girl the fun begins again. Usually I say I'm 18-21.

There's a lot of younger girls there, but this is about a girl I found who's 18. She told me her asl and she ended up being in the same state as me. We narrowed it down closer and closer, until turned out she lives in the same city, about 20 minutes away! I kept an image of the chat record and will post a copy of the conversation, but to summarize it, I told her I was 21 and she really liked the idea of me playing with my toys, and that even she'd like to ride the the long 12" double dildo with me. I tried to get her to text me but she didn't want to give her number out to a stranger. So after we talked a bit more, I asked if she had a toe we could talk on later. That's when omegle crapped out on us with "technical difficulties"!

I was a bit pissed at omegle there but hoped something would happen. I kept scrolling through new partners, pasting my "playing with toys" line, and after a few minutes, I found her again!

Our second conversation went very differently. I found out she has a beautiful name, and from there it went from talking about her little vibrator, to anime, and 50 Shades of Grey. And by the end of a much longer conversation, she decided she was pleasantly surprised and that I wasn't a stranger anymore. She decided she wanted to text now.

That was three nights ago I believe (it's hard to tell because we've been staying up texting til 3-5am each night) and we've been getting very sweet and flirting with each other. Then last night, when she had a sleep over with her cousin, little sister, and a friend all in her bed, our texts started turning into heavy sexting. But she couldn't do anything for being squished between two girls in bed. By the end of the night she was telling me how wet her pussy was for me, that she was in agony not being able to relieve herself, and when she knew how excited she was getting me, she begged me to cumm for her. I did, and after some more flirting, she wanted me to cum again for her, telling me how much she wants to help take care of me and clean me off with her mouth and that I can only imagine what she's going to do when she finally gets real a taste. After she made me cum twice last night, she starts talking about how turned on she got me by thinking about "taking and spanking her naughty ass" (her words) and now I can't wait to find out what's going to happen next.

Now we've been flirting more and more heavily over the days and building up to getting together. She really wanted to see fireworks together and get a fourth of July kiss but we're both too busy that night, so instead now she can't wait for what I told her would be our own personal private fireworks that we could make. But I still have to tell her I'm ten years older than her, not three, and I'm still wondering if she'll love it or hate it. But from our texts, I think it's going to be a good surprise for her.

I'm going to go through the two logs of our chat next and edit out a few details. Then I'll post them for you guys to enjoy too.

But first, just how awesome omegle is... Another girl I met that same day there, that I won't go into much detail about, told me she was a virgin and a bit young, and she was very curious to see what dildos looked like. I toe'd her some pics and videos, telling her how good it feels when she finally get to stretch that pussy and ass to take something. At first she was curious, then said it looked kind of gross and dirty seeing anal for the first time, but shortly after she's asking me to teach her where her clit is and show her more of my toys... now that's a awesome toe log that I'm saving with pics that motherless won't approve of. d:

And that's it for now!

so i have to confess that for 3 to 4 years i was fucking my best friends girlfriend. this is how it all started and some short stories of times we fucked, hope u like and please comment......... let me know if u want more

so ive been friends with this guy since i was like i was 15, back then he was 19 or so and had a girlfriend since a lil before i met him , anyway we used to hang out every day and at one point we lived together in the same house but his girlfriend would come by a visit and most of the time, we would all go out together. i always tought about them as brother and sister at first i wasnt attracted to him or her in any way but i did notice after a while that he was always making comments or saying things trying to see my dick or so idk i never really wanted to do anything with him and always played it stupid like i didnt know what he meant.

it wasnt untill about 5 years ago when i was like 19 or 20 that i started getting soo horny by seen his girlfriend wearing tights seen her lil camel toe and trying to get a glimse of her tits, ass, pussy or anything, i started waking off everyday soooo many times, by this time they bought a trailer home and move in together i would hang out there all the time and sleepover all the time,in the morning on the weekends they would go to work and ill be home alone, one i notice notice they would allways leave their room door locked so curiosity kill the cat right !!! i picked the lock and went in the room for the first time while they were gone, i stared looking at every drawer, found all this sex toys condoms lube, pnties, bras, and all her stuff " ive seen her lean down and u can see her slutty thongs and i remember i just wanted to ripped them off" with my mouth and all the ones i seen her wear were in that lil drawer lol

after that every day when day left i would go in the room and put on her panties and jerk off, weeks past and i started to jerk off and cum all over her panties in the drawer and one day i notice their digital camera on the nite stand, i looked and ther were some hot pictures but nothing really nude. but enough to help me jerk off

by this point i started jerking off sooooooo much and sleeping in just boxers, and since he would live at 7 and she at like 9 if she had to go at all , i started getting up while she was making breakfast" i slept in a couch in the living room but since it was a trailer the living room is right at the kitchen". anyway i would get up and start talking to her and make conversation u know , and at the same time drink coffee with her still waering just boxers so when i sat i wuld pull them up so i knew my dick was visible and since i knew she was looking i would get soo hard so fast. i did this so many times soo many days and as soon as she go to the room or anywhere i would just touch my dick and blow up, once she left her cup to goto the bathroom and i actually put some of my cum in her coffee.

anyway i knew she cheated on him a few times, 4 or 5 to be exact so i knew she was horny and a fucking slut and the pressure was just building up and i wanted to fuck er more and more, while this was happening my friend would keep making this comments like tring to say he wanted to see my dick and shit like that , come on one day he ws like " man this would be perfect " amlike what would be? i said " if we were gay u could be sucking eachothers my dick while one of us drives, and do shit like that at work and nobody would think we are gay cuz they all think we are bros" anyway i was like yeah that would be the best cover lol.

but the one thing that made me say fuckkkk this shit was one nite while we sleeping t i started hearing something moving like a cup on a plate, just a little sound in like waves like bum bum bum so i got up and sneak up to the kitchen 20 feet away and started listening towards their room and then i heard her moaning while she was getting fucked, that nite i was sooo motherfucking hard, so i said am gonna step it up a lil, and once i rubbed my dick on her ass on purpuse and shit like that, i would cum on her tooth brush, on her clothes i woud ask her if she wanted a drink and put ice cubes witch i rubbed on my dick and put cum on them and then put them on the cup.

one night idk why but it hit me, if they had some hot pics on their cam!!! whats on their computer???? so i went and open my computer and typed "jpeg" and all this pics started to appear, i sort thru them and holy shit jackpot there was this whole folder with pics of her naked and him fucking her, i had this adrenaline rush i could not sit still i wanted to jerk off so i did and that wasnt enough i didnt know what to do.

ok so a few days later he had to go to work like 50 miles away so he was gonna spend the nite at a hotel with his coworker and he told me how they were planing to hit up the stripclubs and shit those 3 or 4 nites they were out , so i had to make my move i coulnt hold it anymore, that nite they left i i called him and i said i had to go get some shit from his house so he told me just stay there so his girl wasnt affraid at nite so i was liek idk i got shit to do but maybe ill stay lol curse i was gonna anyway!!!! i got there and we talked for a while and she was on the couch and i was laying on the floor i didnt know how to make my move so while laying on the floor i put my foot up on the couch between her legs but no nowhere near her pussy, i was wearing thos nike sweat pants those saggy big ones no underwear , and she said damm those are big, they look warm and comfortable, i was like yeah they are here am sure u can put ur foot in them and theay will fit along with mine here try it and see how nice they are !! at this point she was down to try it and i remember she was wearing tiny shorts and no sucks, so she start to put her foot in thru the bottom of my sweat pants, keep in mind am still in them , i start feeling her foot and her leg running up againts mine going up my pants and i just got so fucking hard and she was up to my knee so in a joking voice i said dont keep on going cuz u gonna reach my NO flying zone!! adn she just kep on going saying am i there yet now, finally her whole foot was inside the pants along with mine and i say u are soo in my flying zone now just dont turn ur foot sideways cus there is something there, and of curse she turned her foot and just rubbed my dick and just started playing with it with it, i got up and we started kissing and i played with her tits liking them and just touching her but she woulnt let me touch her pussy till finally she gave me a bj and said i would fuck u but am on my period.

that nite we sucked each other and just talked about how bad we both wanted to do it and she told me she used to get so wet all those times she saw my dick during breakfast and all my tissue papers arround the house full of cum i used to leave so she ill pick up , i never told her i had cum on her clothes, tooth brush and even in her coffee. sadly he came back on the third day and thats almost how long it takes for a normal period to go by but nyway it was down hill from there.

he came back monday early like 4am, the next day we started what came to be 4 years of teasing and fucking,the first tiem we fucked was like 3 minutes long lol i just got to his house and started kisisng and fingering her for the first time, she was oo wett her pusy was so soak she was dripping down her legs and her panties were soaked, i call him and was like yo where u at? am at your house hurry up !! he said he was like 5 minutes away, and i was like ooohh fuck so she was putting her pants back on and i looked at her and said idk about u but i have to fuck u right now or am gonna go insane so i just jump on her kissed her and the funny thing was we were both looking down when i was about to put my dick inside her like my dick and her pussy were different people, we both looked down and i put my dick in hher slowly and omg it was the besst feeling ever, we fucked for like 5 minutes and both came then we rushed to get clean up before he got home. after that we started touching eachother eating each other all the time behind his back even when he was like 3 feet away and idk but the fear of getting caught made it 1000 times more interesting and hot here just some times and some things we did

we fucked minutes before he got home almost every day and i would cum in her mouth adn she ill swallow and literally he would walk in sometimes 20 seconds later and they would start making out, sometimes she didnt even get a chance to rinse adn she would wink at me and ill be like omg am soo horny again

he was behind the drier head down behind it hoking up the exhaust pipe and we would be right there with him, me fingering her pussy and she would just grab my dick and put it in her for a few strokes

while in the car as soon as he go out for something i would start eating her anyway i could

we went camping and i ran to the bathroom asked him and her if they had to go and she said i do and we both went, lets just say we had a quickie

while he payed soccer we would fuck around on the bench, touch finger her basically tease eachother

while we worked outside his uncles house i went to get some water inside where she was and finger her and fucked her while we both looked out the window as he worked

a few times we go shoping and while he looked the other way i would grab her ass or tists and if she was wearing a skirt i would just shove my fingers as far in her pussy as i could

at my birthday party i was taking some pictures and she would purpusely pose all sexy and oopen her legs so i can see her pussy covered with a tiny thong

everytime we were at the house we would tease eachother soo much that we were all horny and when he would go to shower or pee or away for anything we literally would jump on each other and fuck or do anything we could

she clean houses for a living so we came up with this idea so we could actually fuck every now and then for hours at a time without been bother or caught , she cleaned this one house every 2 weeks and nobody was ever home, the owners were home maybe 3 months out of the whole year at the most so since her boyfriend " my best friend" knew she cleaned that house every other week i told her to just run it by him and lie saying they asked her to go every week, she did that and we would meet everyother friday at a starbucks and leave my car there and we would take her car to the house and just fuck and fuck for 3 hours evertime, fuck everywhere anywhere anyway we wanted and just fuck and fuck and fuck till we couldn't anymore

one time her lil sister came to visit and while her lil sis was sitting on the couch faceing the tv i was behind the couch sitting at the dinning room table i happened to put the lil cat cage behind the couch so while her lil sister is wtaching tv am RIGHT THERE behind her lil sis siting on a chair, my hand and elbow are right behind her head on the armrest , she comes and pretends to be petting the lil dogs but i pull my dick by the side shorts and starts sucking me me, omfg god here i am wathching a movie talking literally talking to her lil sis while she is sucking my dick, at one point her sister turns arround and i just push her head off my dick and she pretends to be pe petting the cat then goes back to sucking, after that a lil bit later i cum and she just keeps sucking and swallows it all and like nothing happened just goes and sit next to her lil sister.

another time, my friend was taking a shower so while hes in the bathroom" bathroom is down the hallway next to the masters bathroom, the doors are side by side like if ur facing the room door the bathroom door is on the left" anyway he in there taking a shower am all yelling while leaning on the master bedrooms door so am talking to him thru the door and looking inside the room and shes folding clothes on the bed and she starts to play with herself puts her hand in her pants and masturbates tuching her tits and am just watching, then she takes off the pants and spreads her legs on the bed and keeps playing , i can see how wet she is and shes calling me with her hand but shit hes right there and can come out anytime so am hard as fuck and am like fuck fuck fuck and i cant hold it anymore so i just pull my dick out pull her toward the edge of the bed and just tick it in as hard as i could, we both moan in pleasure and i just fuck her as hard as i could but when u are this horny and the risk of getting caught minutes seem hours and the pleasure is something i cant describe, in a matter of 2minutes maybe less we both came and i just put my whole load in her pussy, she took her fingers and put them in her pussy pulling out some of my load and lick it ans said , mmm i love the taste of ur cum an not even 20 sec latter he turn off the water and came out, but not before i could ask her to show e her tits to take a picture

thats the other thing, we loved to take pictures tho i never told her i seen the ones she had taking with him before , but we took hundreds of pictures and videos and thats another story, one day i told her go take some pictures of ur wet pussy so i can go do my self cus that day he was home and havent had a chance to fuck at all so i gave her my phone and she did but later on that day i forgot and left my phone on the counter and he picked it up and was about to look at it adn i was like dude no dont look at my pics, hes like why not!! got some pic of your girl naked or something!!! " adn in my head am thinking no dude but i do have pic of ur girl thats fosho! so i was like dude no but thats not cool, he said allright whatever and handed me the phone lol i almost shit myself lol

but the time we both came without fucking, i literally came in my pants without touching my dick at all, we we were watching a movie the 3 of us, we started sitting in the same couch it was her him and me so we couldnt really do anything cus he was in the middle, i just kept giving him drinks and drinks so he would have to go piss so i had a chance to at least eat her pussy out for a couple of seconds and maybe even fuck her for 2 seconds, he finally did and omg he wasnt even in the bathhroom and i just jump over and started kissing, pull her pants and under wear and put my dick in her stroke it a few times and went down to eat some of her pussy, her pussy was always wet and her pussy lips are big and soo fucking tasty. then we hear the door so we settle down, but by this time he comes by and sits on the floor exacly in the middle of us but on the floor. so she lays on the couch sideways and her as is right there and am on the other side so u put my feet up and start touching rubbing her pussy with my foot , a lil after i was ike fuck it so i grabed my friend and start massaging his neck with my left hand " i know kinda gay but whatever" and am like dude u are tense lol minwhile with my right hand i start touching her legs working my way to her pussy and am just rubbing it over her pants " she was wearing some like sweatpants but made from the same material of yoga pants so it was very easy to move them around, so i just pull them down tilli could see her asshole and put my hand in there and plaid with her pussy and omg she was drriping and i mean soaking wet i kept liking my finger and tasting her juices ans she was just loving it "now remember!! am gayly massaging my friend while am doing this and he has no clue"

while am doing all the i just fell my dick like is gonna burst with cum like it is right now just by remembering it. we never had anal sex i never tough she like to but that night she was so wet and i put my hand in her pants at one point i took my finger and by mistake put it in her asshole about an inch and she jump a lil, i looked at her and she starter biting her lip so am like omg game on, i look and i could see her pussy just dripping and her asshole all shine from her own juices so i took my finger and started playing with the lil ring arround her asshole, at this point her face is fill with pleasure and she closes her eyes so i tap her and am like wtf dont do that cuz hes gonna know, she look's at me i i read her lips going OMG AM GONNA CUMM, so i just stick my whole finger in her ass and 2 in her pussy and idk there is nothing more erotic nothing compares to this, i just keep on kingering both holes with one hand and gayly massaging my friends neck with the other hand, at one point i had 2 finger in her asshole even 3 and she was just about to collapse or something, her pussy was like niagara falls and i took my fingers out of her pussy and ass and leak the one by one as she looked, i keep on fingering her and i swear i just felt my dick bursting with cum while feeling her asshole and pussy as they contracted on the inside as she was cumming then i back away and sat back like nothing had happend, i put my hand in my pants and pull my fore skin all the way so most of the cum would stay in arround my head, and like 10 minutes later my friend went to the bathroom and omg thank god he did cuz she just jump on me and suck my dick dry and just swallow it all, she clean my dick completely and i jus yanked her pants down and eat her pussy and even her asshole witch they were still all wet, and with my finger i pulled the her juices out of her pussy as much as i could, we finish the movie and went to bed.

there aro soo many other encounters but that tv was the last one, all i can say is we got sooo horny that one day it all wnt to shit and i dont have a dest friend anymore and when i see the pictures i wanna go fuck her one more time
ive been texting her but she wont answer so i dont know, you guys tell me would it be too much to go to the house and wait for her to come clean the house and try to get her to fuck or call her and be like if u dont answeer am gonna post our naked picture on the internet and see if she wants to talk then .

some funny things were that she would make out with him seconds after ive cum in her mouth, i found a bunch of gay porn on his computer and he always made his wierd ass comments, apparently he would fuck her but was just boring for her and the one thing he complain about was that she never got wet , hens the lube in the room but with me, am telling u guys this girl was always dripping with her juices soaking her panties if any and more then 10 times i saw her dripping on the side of her legs

** Caution Gay sex ahead **

Quick Story Details:
I'm 38 Married 6'2" 212lbs fit, dabbled with some Bi stuff as a teenager, never did anything more than mustal hand jobs
Guy in question, My neighbors Son, 20 5'7" 150lbs? Trainer at a gym and is in incredible shape, 100% Gay

My wife is away on Girls weekend to Atlantic City, I just got back from a business trip. Neighbors Son, Jeremy is watching our dog. I come home a little earlier than expected about 9PM, and can't wait to hit my Jacuzzi after a long travel day. I come in, drop off my suitcases in the laundry room, strip down and stroll on out to the deck to the Jacuzzi where I see Jeremy hanging out with one of my beers in his hand!

We were both shocked. I just stood there naked like wtf and he tosses the beer and acts all embarrassed. I finally speak first and say...wth man, that's alcohol abuse, stay there. I go to he fridge grab 2 beers and come back and hand him one and tell him he's earned it for watching the dog. I then get in the Jacuzzi with him,

He's quiet for awhile and I'm just sighing, and relaxing, and he finally speaks up..."I hope you don't mind that I'm here, I thought you might be pissed!" I said, "No not at all, me Casa su Casa" It's then I noticed his clothes were on the chair next to the patio table. so I said..."Naked too huh?" He says, "yeah, I let Lucy out and it looked inviting, so I stripped down and came in" I said, don't worry about it, Baths are made to be Naked. You don't shower with a bathing suit on do ya?" he laughed..

We chatted more for about an hour each getting out here and there to piss and get more beers, but I won't bore you with that BS..

We get to talking about sex lives, and he's wondering how I handle long business trips with no sex, and I say, well I look forward to coming home and getting a BJ from the wife and fucking until the sun come's up, but unfortunately, she's not home, so I have to wait another day!"

He says, too bad you're not gay, because I've been staring at your cock all night, and I'd be happy to give you a BJ right now if you asked me!!

I admit I was little uncomfortable for about 3seconds, and then I lifted myself up to the end of the tub and sat down and told him....go for it...

He launched himself across the tub so fast that wave of water came up over the side along with him, as he hungrily sucked my cock, which was already hard, right into his mouth.

I never got a BJ from a guy before....he knew what to do!!

He was sucking, and stroking, and moaning, cupping my balls, kneeding them, taking me deep into the back of his throat, swallowing as much of me as he could fit. (proud 9.25") I told him I was going to cum soon....and he stops sucking me and squeezes my cock tight, looks up at me and says NOT YET!

He gets up goes to his clothes and back-pack and gets what looked like hand lotion. I could see his hard cock bouncing as he moved back and forth. he comes back and says, "I know that Maria (wife) doesn't like you to fuck her ass, (which is true, she'll do it, but she's not a fan at all!!) so now is your chance to fuck an ass HARD!!"

He gets back in the tub and bends over the side, takes the lotion and covers his asshole with it. I get behind him and press my hard cock against his hole, He says, Let Me, and he holds my cock steady in his hand as he rocks his ass back and forth on me getting it in ...working that hole open. I'm watching as my head presses in and out and in and out. He finally presses back more and my head pops all the way in...He let's out a "ohhhhh Goddd" and continues to press into me. (Holy shit was it tight!) He moves back right up to my balls, so slowly, and keeps saying, Fuckkk Fuckkkkk omg fuckkkk. He tells me not to move and I just stand there as we stand connected. He finally starts to move a little, and then a little more, eventually he's taking me out to my head and back down to the balls,,,slow at first but now faster. I'm just watching my huge cock disappear in that hole. He finally says...NOW, Do it now...fuck me Hard as you can!!!

Without hesitation I grabbed his hips and slammed into him. he started moaning so loud that he grabbed the towel we were using to dry off and stuffed it in his mouth to muffle his moans. I could feel my balls building but kept trying to hold back, wanting it to last longer. (Football Baseball, ice dancing, Naked Rosanne Barr, anything!!) I fucked him HARD for what seemed like a good 10minutes. I could feel him jerking his cock under us. I finally said.....I'm going to cum...He muffled,,,,CUMMM IN MEEE. I was cumming before he even got the last word out.....I pushed my cock as deep as I could get it and filled his ass with cum.

I stood there for while, expecting my erection to subside, but I was still rock hard, like I took a Viagra or something. Jeremy started to push back on me, I thought maybe he was trying to push me out, but instead I reached under him, and pulled him back to me and sat down back inside the Jacuzzi with me in his ass on my lap... I reached around and stroked his hard cock underwater.

He just said, fuckkk yes and started to grind his ass on my cock as I jerked him. I kept alternating hands, right hand, then left, then both...He'd bounce on my cock and then grind, and twist and make circular motions...I was still hard and I could feel cum building again. I jerked him faster and faster, he started convulsing and grinding on me faster...the waves in the tub were starting to be a problem...but finally he says....Fuckkkkk I'm cumming....and I could feel the cum pulse through his cock in my grip. With each pulse he'd thrust his hips upward and his ass would grip my cock and pull it so hard that I came in his ass for a 2nd time no more than 5seconds after he finished cumming.

This time, my cock subsided almost instantly and it worked its way out of his ass, along with a river of cum.

We both immediately got out of the tub and dried off, both out of breath and not saying a word. I finally said...Looks like I'll have to drain the tub. He said, well I'll come by to help if you need it.

I said, sure, but please know that this is our little secret, He assured me, that mums the word, and added..."Btw, have you ever had a cock in your ass?" I said, No, I just don't see me doing that, I may have to just draw the line at receiving a BJ and being the top to your bottom (with a laugh) " He said he'd be OK with that, and he left.

The following night my wife was home and we fucked until the sun came up per usual, but I have to admit....when I talked her into anal, I couldn't help but notice that Jeremy's ass seemed tighter than hers! I could just chalk it up to different lube, or her ass being used to my cock, but it was an odd realization. But once she took the toy in her pussy for some DP, that ass tightened up like a drum and I came HARD!

I admit that I want to fuck Jeremy again. I might even try a cock in my ass. Not sure. But definitely not in my mouth. I still prefer the taste of pussy vs cock!