So I've always wanted to have group sex with my girlfriend. She is 20 and I'm 22, we've been dating for about five years. We have several dildos that we use occasionally. I managed to convince her last night that over the weekend I had arranged a gang bang for her.

I have electrical tape, a ballgag, a blindfold, and ear plugs. I've explained to her that once she is immobilized and unable to see or hear that we are going to each take turns on her. I am hoping that with using condoms on the dildos (non latex) and her being sensory deprived/tipsy that she will genuinely believe multiple people are taking turns stretching her out.

I plan to fuck her first then "as each guy takes a turn" I'll be changing clothing quickly and putting the condom on the dildo and put it through the zipper of whatever pants I put on. I don't know if the condoms will make it feel real though. I'm looking for any suggestions as to what to do to make her believe it's actually happening.

If it comes down to it maybe I will get a few guys and pass her around but that would have to be for another time.

My wife's niece is staying with us for the summer while she is on break from college since her dad and mom are presently stationed overseas for work. She isn't what I would call super hot, but she is attractive and curvy in all the right places and I can't stop thinking about her. Probably mostly to do with her just being a young, carefree college girl more than anything else. Her and some of her friends were lounging by our backyard pool this weekend and I couldn't take it anymore, so I had to go inside and jerk off thinking about all of them. It reminded me of the scene in fast times where he is jerking off watching the girl from the bathroom window. God I miss being young and having a tight bodied female to fuck.

Well, I work from home and nobody else is around during the day so today curiosity got the better of me. I went into the guest room where she is staying and started going through all her stuff. Mostly pretty typical. Some underwear from tame all the way to thongs and lingerie. Definitely sniffed her dirty panties in the laundry basket, god they smell so good. And then I found the motherload in a large shoebox that knee-high boots would typically come in that I found in the closet. Multiple vibrators, dildos and butt plugs, an eye mask, cuffs, a little feather whip thing, and a strap-on harness! I am floored. I knew she is clearly sexually active, but wasn't expecting this. So I know this part isn't for everyone, it is just my taste, but I can't contain myself and as I type this I am rock hard sitting in my office chair with one of her vibrators on full in my ass. I love ass-play but knowing it is her vibrator and maybe, just maybe it will be in her pussy tonight is such a rush. I am going to cum buckets any minute!

I'm living with my uncle for now while I go to college. I was using his computer last night since mine became worthless from multiple viruses. I started snooping through some of his files with some obscure names that peaked my curiosity.
Holy shit! I didn't know my uncle was gay. Tons of dick pics, gay porn, and some videos of him jacking off while shoving a big ole dildo in his ass. I never would have thought it. I've seen him with girls just not any recently. He's a manly man.
I don't really pay attention to dudes, but I don't mind seeing how and what gets other people off. I didn't look at every video mainly, cuz I didn't want to get caught.
Before I went back to doing some homework. I emailed myself a video of him in our shower with a dildo stuck on the wall.
After I finished my homework I went to my room and checked my email on my phone.
I've seen my uncles body, but not naked. He's a 6 foot muscular Latino. He's pretty fit from working construction since he was 18.
The faces my uncle made while he backed into that dildo on the wall, while his 8 inch thick uncut cock hit his stomach.
Watching him enjoy himself so much, and stroke his cock. got me so hard and leaking precum from my own uncut cock. Mine isn't as thick as my uncles, but it's just as long.

Forgive me if this isn't written like a well written story. My mind is blown. I just found out my uncle is gay, and I shot one of my biggest loads watching my uncle twerk his ass onto a dildo in the shower we both use.
I don't think of myself as gay, but seeing how much he enjoyed getting off with a fake cock inside him. I wonder how he acts when he has a real one inside.
I know when I jack off later tonight I'm probably going to stick a finger in my ass, and I'm probably going to like it. and when my uncle goes to work tomorrow I'm probably going to make myself a copy of his vids so I can take my time watching them all.

With as much porn as I watch, and thinking about sex like 90% of the time. I have a feeling I'm going to have give an update on this post soon.

I have always loved to develop a woman, sexually, make her comfortable doing things, she wasnt ready to do when we met.

I did this on multiple occasions, sometimes with success, and many times this lead to the demise of my relationships, but every time, it was a fun ride.

For instance, my college gf, didnt like cum, but ended up as a cum hungry bitch, who would, in the end, be disapointed if we had sex without a cum play.

My ex wife, total prude, from being body self aware, to wearing no panties, sunbathing topless, and sucking and fucking in public parks, on parking lots, in the cinema...

My newest conquest is this divorced woman, my age (early 40s). Successful doctor, cardiologist, her marriage collapsed due to long working hours, so we started off as fuck buddies. Still slim, still hot, brunette, she got a boob job soon after we started messing around (and right after her divorce).

For a woman of that age, she is, of course, experienced, but like all, she had her weakness. When she was on top of me, I reached with my hand towards her anus, wanting to stimulate it with my finger, and she moved my hand.

It took me over a year, but gradually, I made her enjoy her asshole being used.

I started by licking it. It wasnt that easy, she moved away at first, but one time, I offered her a foot massage. She was on her stomach, as I massaged her, until she felt totally comfortable. I would move her legs aside, so that her pussy and asshole were visible to me. Moved my hands up, and started working her clit with my hands, while my cheek was pressed against hers. As she was close to orgasm, I moved in a way, that she could feel my breath on her asshole, and she started arching back, so I went for it - she came instantly.

This was a thing for a while, and the next step was the finger. By that time, I introduced dirty talk, and as she was on top of me, I was just telling her what a great cock rider she is, and pushed my finger in her mouth, asking her, if she is a bad, bad girl. She noded yes. Are you sure? Again yes. With my left hand, I moved her cheek to the side, she knew what was up, and as I moved my wet finger back, she followed it with her eyes, as far as she could. I didnt go in, just started rubbing the exit - she came like she was obsessed.

Then, slowly, things moved along. It was a finger, then two, and when I showed her the first but plug I bought, a small one, she smiled.

Soon enough, I was fucking her in the ass, and she loved it.

But that wasnt enough.

Again, she was on top, with a plug in her ass, when I decided to pull it out. She was moaning from joy, as I spread her cheeks wide, knowing her asshole is gaping back there. "you want a cock in your ass, right now, dont you?" Of course she did, so I put the plug back in, and again, she came like crazy.

The plug was substituted with a dildo, then a bigger one, until double penetration became something normal for us. And every time, I was telling her, that she needs another cock to be completed, and she would shiver in extasy.

The night I invited my friend over, after we were in a local bar, to join us at my place, while we were going up the stairs, behind him, I whispered to her "he is here to complete you".

She almost fell, but kept going up.

He knew why he is there, we did all sorts of things together, and this wasnt our first rodeo, so as soon as we came in, I started undressing her, and kissing her, and she was ready.

It was like when we practiced - her on top, only this time, it was another mans cock up her ass.

It was unbelievable.

Tomorrow morning, she told me, that it was great, but that she feels ashamed, and that we shall never do it again. I said ok, but I know that that was a lie.

Will keep you posted.

Well since I can't tell my wife about it I guess I will just have to get it out on here. Yesterday on my way home from work I was contacted by a guy who I have met before on Grindr. Since I'm only in the area he lives in once in awhile I said I would stop by and see him. When I got to the apartment complex I got my sissy bag together with what I was going to wear for him. Since I already had on my bra and panties and my breast forms I put in a cute little short yellow dress and my wig along with my poppers. Went up to the apartment and he answered the door and led me to the bathroom to get changed. I had forgotten how much bigger this black man was then me. Stands a good 6 inches taller and definitely more muscle than me. I go and get dressed for him and meet him in his bedroom. He always likes the fact that I stay shaved smooth. I sit down on the bed as he pulls out his hardening cock as he is walking around to me. I take a big hit off the poppers and swallow his dick. I work in and out as it gets bigger and bigger. I only stop to hit the bottle a couple times as he is guiding my head and sliding his hard cock deeper and deeper down my throat. After a little while he stops me and tells me to get on the bed with my ass in the air. I bend over as he slides my dress up over my ass and rubs his 10 inch cock up and down my ass. As he starts to slide into me I hit the poppers a few times and feel the rush of them as he buries his dick deep in one stroke. God I missed that. It felt so good damn good feeling him inside my asspussy. He kept telling me how much he missed my pussy and how good it felt. The next 20 minutes are kind of a blur as I kept hitting the poppers hard as he kept fucking my pussy even harder. I lost track of how many times he came inside me. I definitely came multiple times from it. When he was finally done I went and got changed before I left. I made sure to thank him for the breeding he gave me and I definitely wish I could get it more often. On my way home afterwards I was still so horny from it I had to stop again and fuck myself with my black 13 inch dildo and came a few more times before heading home to the wife. God I love taking big black dick in my ass pussy. 

I confess i want to watch my wife used by other men. Fucked in all 3 holes by multiple big dicks and her pussy filled with cum. After, i want to eat, lick, then fuck her stretched out, cum filled pussy.

I love fucking her after ive worked her over with a few big dildos. She cums so hard and occasionally squirts when shes filled with those big dildos . Her pussy feels so good after its been fucked and stretched like that and my average size dick almost gets lost in there when its like that.

Should i tell her i want her to enjoy a few new big cocks.

Normal back and forth at a bar. Made a bet I'd break her first. Friendly wager. Whomever broke first had to give the other oral. If they broke twice they'd take it up the ass. She was excited, thought she'd get to peg me.

I confess, I cheated. I jerked so long and so hard before hitting the bar that there was nothing in the tank. Took almost no time to break her the first time. She's a squirter, it's pretty obvious. She hates blowjobs, doesn't suck dick, doesn't matter a bet's a bet.  Before we start I break out her toys and lube. Did need the lube but used it anyways. Mouthful of cock, worked her hard with her dildo before moving to her vibe. She never stood a chance. Look of fear as she squirted with my cock still in her mouth. Now sucking furiously but it's not happening. We both know she lost again. She gets rolled and bent.  More lube, kept her vibe in and kept working her. She's shivering slightly. Finger for a few to work the lube in and loosen her. Eventually work my cock in her ass. Slow, gentle, vibe still going strong in the other hole. No friction, it's sliding good but she's never done anal, it's tight. Takes more time but I get her to relax. Finally she's losing her brown cherry. I fuck it good. Tears, moans, admits it's in her ass. And I feel it building. No joke it's building. A few more thrusts. Literally balls deep, she screams, begging to stop, to take it out and I just nut. Biggest, deepest load I've ever blown in a chick. She's sobbing and in tears. I'm flying high and stunned because I have no clue how my body magically made multiple loads. She's completely fucking broken and her face bears the shame. She knows this was a whore fucking, she got owned. No photos, because if I lost I didn't want photos either!