[MF] My wife’s first anal adventure (Just a vibe this time)

A couple weeks ago, me and my wife got home from a date night out a little buzzed. I walk into our kitchen to get a drink of water and turn around and realize she’s gone to the bedroom.

I walk down our hallway to the bedroom and see her laying fully naked in our bed except for a tiny little thong, lightly rubbing herself. This isn’t wholly out of the ordinary but I was feeling pretty excited to see her so ready to go.

So I pull off my clothes and we start making out while I caress his breasts and slowly make my way down to her panties, slip my hand in and feel she’s already wet. Since she’s already so ready, I decide she should help me get on her level. So we switch positions and to my surprise she rotates her body and rolls over so that she’s on her back with her head hanging off the bed and grabs my cock and pulls it into her mouth.

[MF] From strangers to anal in less than an hour

This happened a few years ago, and remains one of the most random encounters I’ve had. Because of the timeline of events, there isn’t much back story at all.

I had spent the day out bar hopping with different groups of friends. Being in a big city, it’s easy when you don’t have to worry about driving from place to place. Finally, a bit after midnight I decided I’d had enough for one day and it was time to call it quits. By this time I’d accepted the fact that I was also going to be going home alone.

Being a nice night, and only about a half mile from home, I decided to walk home. About a block from my apartment, a cab pulls up to the curb slightly ahead of me and the rear door swings open. As I walked by, I glanced over and saw a cute brunette paying her fare. My eyes lingered a bit as her dress rode up her thighs when she leaned forward to get her change. She caught me looking, but I didn’t really care or think anything of it.

Mutual sucking with a straight, virgin crossdresser [MT] [M29,T20]

A couple of weeks ago I was browsing a fetish social network and saw there was a new user in my area. A crossdresser calling herself Lara, 20 years old, slim, 5’9”. There were two pictures, one of her ass in a black thong, showing a nice muscular ass, not hugely feminine, but more androgynous. There was a second photo or her crotch from the front, in black satin panties with a slight bulge and just the smallest hint of her cock head. She said she had no experience with guys and was looking to try everything from kissing to anal, but lived with her parents so couldn’t host.

I messaged her right away and we began chatting. Over the course of the coming days I found she was “straight” – or as straight as you can be when she’s telling me she wants a man to fuck her in the ass while dressed in her sisters clothes. We chatted back and forth for a bit and built up a good rapport. Eventually I suggested we meet last Friday night. She was kind of cagey about meeting, but did agree that we would meet at a car park close to my home and chat, before going to my house after if she was comfortable.

My first time ever (f) at trying DAP and DPP [mmf]

Hello there, I am back for some more stories! I shared my first ever gangbang a couple of weeks ago (check it out here if you are curious: https://www.reddit.com/r/gonewildstories/comments/6ibaks/my_first_ever_and_not_the_last_gangbang_group/ ) and I promised more stories so here is another one that might be pretty interesting as well. It was the first time I ever tried DAP (Double Anal Penetration) and DPP (Douple Pussy Penetration).

It was something that interested me for a while, a couple of months after my gangbang, I started looking at porn videos of gangbangs just for inspiration. And just watching them made me even more curious about some of the stuff they do. Two of them is having two dicks in my pussy and two dicks in my ass. Since the first time I saw it on the screen, I always wondered what it felt like and if it was possible with me!

So as you may know already from my first story, I have 2fwb where I do plenty of 3somes with them both. So I just shoot the idea to them, why not try it? And they were immediately willing to try it, since it was also something that they wanted to try at one point.

[MM] I always knew I would like it in the ass

I had some amazing sex today. I’m bi, but lean more straight. But I occasionally get this insane craving for a big dick in my ass. I don’t have any regular male partners, so I have to resort to Craigslist or Tinder to get myself stuffed.
I’ve been in one of these moments of intense dick craving, so I posted an ad on CL. I got one interesting response from an extremely attractive gentleman with a cock that is big enough to have made me nervous. So we go back and forth a bit, then set up a time to meet. I get there a few minutes early so I park around the corner and Internet for a few minutes. Out of nowhere, I feel a bubble in my belly so I try to let it squeak out. I gambled and lost (never rust a fart). A little bit of goo came out. I felt it immediately. By some stroke of luck, I had some napkins in my car. So here I am, parked in a nice, residential neighborhood on Chicago’s north side, frantically undoing my pants and putting napkins down the back to eliminate all traces of evidence. I decide quickly that I’ll go to the bathroom, find a wash cloth, and freshen up.
Everything feels okay so I walk to M’s place. He answers the door and is fucking gorgeous. More attractive than the photos he sent me. And he’s humble. And intelligent. And an absolutely incredible listener.
We introduce ourselves and shake hands. He invites me in. I ask to use the bathroom. He directs me there. This considerate motherfucker has a box of baby wipes just sitting on his toilet. So I sit down and get everything else out. I wipe. I clean up with the baby wipes. I check my underwear and there is nothing on them! Holy shit, this is amazing!
So I exit the bathroom, walk with him into the bedroom, then lay down and pull him on top of me. He starts kissing my neck. It is fucking amazing. He’s confident and dominant. It gets better. Clothes come off.
I start sucking his dick. This is the first time in my life that I enjoy sucking a dick that isn’t strapped onto a woman. It’s huge. He pushes it down my throat. I gag. He does it again. I gag again. I’m loving every filthy second of this – moaning, squirming as he fingers my asshole, sucking his dick and his balls. It’s all fucking wonderful.
He pulls back, adjusts my position, puts on a condom, and lubes up that fucking hog. I tell him to go slow at first. He just pushes the head in. I’m sure I moan like a whore at this point. He starts with tiny little thrusts that border on pleasure and pain (I like that border. A lot.). I ask for more lube. He obliges and pushes deeper, stretching my poor, tight little asshole out even further. At this point, I’ve got maybe half of this 8 inch cock in my ass (it’s thicker than my wrist, too, so I’m particularly impressed with myself). He keeps going with the small thrusts. Then they get bigger. And faster. And now I’m in full on ecstasy – moaning, grabbing at sheets, praying that my asshole is strong enough or supple enough to take this whole dick. I want the dick, the whole dick, and nothing but the dick! I’m still on my back when he pushes in further. I yelp a little. He tells me to lay on my side. So I do. He’s not getting nearly as deep as I want him to be. It feels like he’s just tipping me. So I suggest that I lay on my belly. He pulls out in the position switch and I can feel my asshole starting to gape already.
He gets on top of me and slides in. All. The. Way. It hurts so good. I have this monster cock in my ass and all I want is for him to fuck the ever-loving shit out of me! And did he ever! He starts thrusting his entire length in and out of me slowly. When he gets all the way in, he puts an extra bit of pressure down. Again, it hurts so good. He starts pounding me. Hard. And fast. It is incredible. He slows down. He speeds up. It’s like he is reading my mind. I’m having orgasm after orgasm after orgasm. I may have ejaculated. I may not have. Either way it doesn’t matter because I’m having the most pleasurable butt sex I’ve ever received. I’m somewhere between orgasm one and orgasm 1053 when I feel. A little gurgle in my belly, making its way south. I knew what it was. I tried to hold it in, but he went from slow and gentle to literally fucking my brains out. I let it slip out. More shit-goo. He’s pounding away and I know what’s happening and I don’t give a flying fuck because I’m having the time of my life. He finally slows down and tells me that is getting a little messy back there.
This fucking guy handles this shit like a champ. He just gets up, goes to the bathroom, cleans himself up, then comes back with the baby wipes! I clean the santorum off of my legs/ass, we put a towel under me, he puts on another condom and keeps going. I’m in awe of the facts that this dude hasn’t come, yet, and that his dick is still hard. So I go with it. He keeps going hard and fast, then slow and gentle. I’m finally on all-fours and this beautiful bastard is fuck-pounding me! As hard as he can. And I’m taking every last but of that beautiful dick that, an hour earlier, I was certain would rip me squarely in half. Seriously, though, he fucked me for at least an hour, probably more. It got to the point that I told him that I needed a break. He asked if I could handle five more minutes so he could come. So I told him I could. I laid down flat on my belly and arched my back really deep so he could slide in all the way. Then I squeezed my asshole as tight as I could (which, at this point, wasn’t very tight at all due to the anal destruction that I had been and was experiencing) and I squeezed my ass cheeks together as hard as I could. He goes into fast and hard mode and comes.
He pulls out. I get up to go to the bathroom and have some trouble walking. I felt like I was drunk. Upon speaking, I learned that I had been fucked stupid. Coherent sentences were not an option. So anyway, I go clean up and head back to the bedroom to get dressed. We chat. I want to do it again soon. He agrees. Keep your fingers crossed.
Now that I’ve been home relaxing for a couple hours, I can still feel my asshole throbbing as if I’m still getting fucked. Also, I’m stretched out. A lot. So I made myself a makeshift maxi pad out of toilet paper and stuck it between my butt cheeks and held it in place with some tight underwear to catch any leaks in the night.
Anyway, I hope you all get fucked as good as I got fucked!

[mF] Vacation Fun With My New Step Family

Quick Recap: Part 1- I’m on vacation with my father, his fiancee, and her daughter. The daughter, Liz, surprises me in the shower. She tosses my salad and jerks me off while fingering my ass. Part 2- After the shower, Liz wants me to perform oral (anal & vaginal) on her but puts a cock cage on my dick so I can’t get off while pleasuring her. Part 3- Liz & I meet up with our parents for a day of sailing. My father needs to leave unexpectedly. Liz and her mom, Trish, want to tan fully nude. Trish explain her feelings on sex and tells me her and my father swing. Then she asks to see my cock in the chastity device. I show her, reluctantly. She notices that it’s too restrictive and cutting bloodflow off. Liz offers me reward for play her game. I tell her I tell her I want to fuck her. Her mother watches us while fingering herself .

Fun with my assistant part I [MF] [bdsm] [rape] [anal] [impact play]

Eliza gripped the white leather armrest as the Gulfstream lurches, the wheels screeching as they meet the cold tarmac. Eight trips in as many weeks and she still isn’t accustomed to flying. She leans forward, her auburn locks falling over her face, as she tries to control her breathing. The plane is a modified G650 owned by Jones & Hastings L.L.C., the large law firm where she was employed as personal assistant to Brian Jones. The cabin had been stripped down to only allow seating for eight in order to make room for the large conference table in the rear of the plane.

Mr. Jones looked up from the papers spread on the table, “For Christ’s sake Elli, I thought you took some fucking dramamine before we left Chicago.”

“I did,” she replies. God she hated it when he called her Elli. Of all the iterations of her name, Elli was the one that made her hair stand on end. It was what her bastard of an ex-boyfriend used to call her.

“Well go to the bathroom and get yourself together. This is a huge case and I need you to be on point.”

It is definitely possible for a woman to enjoy anal, more instructional than story

So, I’m new to the concept of anal pleasure, and honestly thought it was a myth that women actually liked it. Then I met my sweet, sexy, skilled, and considerate lover, and, well, let’s just say I’ve learned some things.

Assplay usually comes during round 2. After we’ve had a quickie first time, we fall back into serious making out – long, slow, deep kisses. He gently rubs and kisses my nipples and strokes my back, and eventually pulls my knee up high over his hip for better access between my legs. I’m a squirter, so with that and his semen, my labia is super slippery, and his fingers gliding slowly from my clit, all over my pussy, and down to my perineum feels fantastic. I orgasm most easily from penetration, but usually he’ll gently rub my clit first – firm pressure in tiny, slow circles – to make me cum that way before sliding a finger or 2 inside me. Then he finds my a-spot (if you’re not familiar, it’s like the g-spot’s less-inhibited cousin, further back), and rubs that hard and fast until I flood his hand with natural lubrication that’s almost the consistency of warm honey and I orgasm so intensely, it sometimes makes me cry.

After a week away,[M]y wi[F]e surprises me with a treat. (Oral, anal)

I’m not the best writer, but I’ll do what I can.
I was away from home for a week with some friends, leaving my wife behind. I’m gonna preface with I’m an ass man. Love ass, love butts, love it all.

I came home late after the trip, which was a 14 hour drive home in one shot. Right when I get into bed, the wife spoons into me, which she rarely does. she’s not a big fan of assplay, but knows I love it and how crazy it drives me.

The next day, standard routine day off together stuff. Groceries, laundry etc. At one point I Say how much I’ve “missed her” to which she cooly replies “Oh, you’re gonna fuck me tonight”.
———— the good stuff ———————————-

We get down to the deed. She’s a plump woman, large breasts and ass. She’s wearing a pair of silk panties that cover her ass and a corset to cover the rest with thigh highs. I’m blown away as I enter the room after a shower, not expecting this treat.
I get into bed, laying on my back, when she puts one thigh over me and the rest of her body on me, her breast almost spilling onto me.

A Walk in the Park, Part 1 [MF][Voy][exh]

Jeanna walked into the room, we’d been having sex for weeks now and I was not getting tired of it any time soon. Medium height, blonde, great ass, and tits that filled your hands and threatened to spill out of many of the shirts she wore around me.

 

“Are you ready to try something new? A little more exotic?” I asked her.

 

“Sure am, I have the day off from work- so I’m all yours.” She said huskily. Already in the mood.

 

Unbeknownst to her I had been recording our last several sessions and converted them into audio files, I had them loaded onto my phone and they were ready to go.

 

She walked over to me and sat in my lap, hands roaming around my crotch. I felt up her shirt and grasped a solid handful of breast- nipple pinched between my index and middle finger.

 

“Why don’t you get out of these clothes for me?” I suggested, she immediately got up- mischief in her eyes as she toyed with the edge of her shirt.