I found a couple that wanted to try an MMF threesome. It took a long time, a quite a few nights of chatting and sexting to get them to meet up. After that, it was several meet ups, drinks, talks, all this lasted for months.

She is a timid house wife looking woman, around 40, short hair, pretty ugly, but with a great body. I honestly thought it will be uncomfortable, and odd (I have never done this before either), and that it will be one big mistake.

Oh boy, was I wrong.

She is the nastiest woman on the face of the earth. She was a bit careful, at first, but after that...

She licked my ass, form behind, while her husband was fucking her doggy style. We did DP, slapping, name calling, you name it...

And they keep coming back for more.

And I am no stud, just a normal guy, normal size, normal stamina...

I think I just hit the jack pot.

Went out last night with my buddy and his friend to celebrate his birthday. Met two girls at one of the club's. My buddy and his friend took one to the hotel and i took the other one dancing and then to the hotel we get into the room and my buddy is fucking the girl and his buddy is gone. Her friend gets kinda pissed i start fooling around with her and get her pants off and she freaks and leaves. The other girl asks nee to walk her to her car and she wanted me to join in on their fun. So i do that and come back and new and buddy end up smashing her like a dirty whore. She ate my ass we dp'd her fucked her throatand she loved it. We both busted on her face and ass twice. Then the other buddy shows back up so we start again. Thus girl got fycked for 6hrs by us. She squirts too. The confession is that me and the buddy are both married. We didn't get her contact number but if I see this whore again ill find the nearest dark corner and treat her like a filthy whore again. I have some video of the action but i won't be able to edit and post for a while

I confess I have fantasies about being a half man/half woman combo with all the best parts attached and being DP'd.

Longer version -

I would love to know what it feels like to be double penetrated as a hybrid man/woman, and could experience clitoral stimulation and prostate gland stimulation.

I had a dream last night where I was a woman around 5ft tall, and I had a big sexy shemale girlfriend. I began riding her cock while my rubbing my clit, and then another shemale comes in out of no where and starts fucking my ass.

Thinking of it just gets me rock solid so quickly. Imagine it?

My wife says she wants to be cummed in by me and another guy over and over in this outfit she's shy but in bed she's a total cumslut and wants to be treated like a whore. She wants to do anything except ass to mouth. Including swallowing and dp as long as we both cum in her. It turns her on A LOT when she hears or reads what other guys would do to her in a threesome with us or what guys think of her.

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

It's not a like super big confession or anything but I think I had a hand in getting my friend addicted to anal.

Basically a few years back me and my wife and my good friend, let's call him Ben. We were drinking and one thing led to another and we ended up with the idea of a threesome. Now this was everyone's first threesome but my wife is no stranger to anal as it is a part of our sex life so we thought DP would be fun. So I took my wife's pussy and we let him take her ass. He was all for it because he never tried it before and well she was all for letting him.  She wash on the pill so i came in her ass, he couldn't really get a good position during the DP so I him finish off in her ass solo and he seemed to really enjoy it.

Fast forward to present day, my wife is good friends with his fiancee. I guess I'm not supposed to know this,  but she told my wife in confidence that Ben is like addicted to anal. She says she doesn't mind as she can get off from it but that she never seen anyone like the ass that much. 

So that's basically that, i think my wife ass opened the anal gateway for him. 

DP for the wife with an 8 in dildo up her ass. Hearing her say she loves 2 cocks in her makes me come.