Tag: Anal

With the boss during Christmas [mmf]

My boss asked me to stay with him during the Christmas break and I agreed. Things at the apartment are kinda going south and since my boyfriend broke up with me, I didn’t want to be alone either. We had off work the 24th-26th, after work on the 23rd, we go to a bar for some drinks.

We start drinking, me more than him and end up after not much conversation making out at the bar table. I end up flashing some of the people my ass because my dress was really short and I’m sure you know, I don’t wear panties unless told to. We go to his place and hook up until he gets off. He wanted to cuddle, which is odd for him but I play along, grabbing his penis and slowly stroking it while talking to him. He rubs my side and grabs my ass then starts making out with me again, I ask him for it in my pussy and he delivered. Since he recently got off, he lasted a lot longer and I got off which felt great. We drink a little more and apparently I passed out. Read more »

[FM] [kink] Body Swapping

I had long had a fetish with body swapping. I.E. trying to experience totally what a women feels like having anal sex. I wanted to take pegging to a new level with a FWB that I met on rare occasions that was similarly wired. Cross dressing was well practiced. She would often shop for me at lingerie sales and surprise me with new items.

I recall one of the few forays into makeup play. You had shown up
with a new bra and several new panties, but was most unsettling was a small, gold cardboard box that had some jewelry, and lipstick in it that you brought along.

What was particularly disturbing about it was that it wasn’t simply
items that you had picked up on sale at a CVS or other discount
place, but rather things you had obviously worn or used yourself
that you were going to put on me. Even though I knew they were
castoffs of yours, it somehow felt too intimate that you were going
to see me wearing them. It also flew through my mind that each
time before I fucked you, you always took off all of your jewelry.
Watch, earrings, all came off. But….I was going to be dressed up
before you inevitably fucked me with the strap on. Read more »

I [F]ucked [M]y wife of 32 years in the ass last night for the first time

I have never written before but felt like I needed to tell this story (true).
A little background about us. My wife (Kim) of 32 years is slim, 5’7″ with black hair and long legs that come together at a neatly trimmed bush. I am 5’5′ and rather well endowed. We have always experienced a great sex life and last night was one to remember.
We had enjoyed a quiet evening at home and after a nice dinner we relaxed and had a few drinks. I had a shower and she did the same. After my shower I retired to the bedroom. Kim had been bathing for a while and to me that is a sign that I was going to get laid. I put on some porn and grabbed a few toys. Soon after Kim entered the room and I could see that she had taken care while trimming around her pussy. Neatly bare from just above her clit to her asshole. She laid down beside me on the bed and we began to touch and kiss each other. I could tell that she was getting aroused. Her nipples were like little torpedos. I grabbed a nipple clip and placed it on one of her nipples. She let out a brief moan as I placed the second one. We continued with fondling each other and getting more and more worked up. As I made my way down her neck she began rubbing her hard engorged nipples. I continued down the front of her stopping to tease her nipples with my tongue. By the time I reached her slit it was warm and oozing with her sweet pussy juice. I couldn’t wait to have a taste and neither could she. I began rubbing her clit and slowly worked my finger into her wet void. Kim grabbed my hand and brought it to her mouth to taste her own pussy juice. I then made my way to her clit with my tongue. It seemed to have a mind of its own and was circling her clit instinctively. I began to suck on her clit and she heaved her hips up. Continuing to work over her clit Kim began to get off. I pushed my tongue into her pussy and she erupted in pleasure. I tried to take in all of her glistening goodness with my mouth as I could. At this point I could tell that she was really getting into the experience. She rolled up on top of me and began to suck my nipples and an occasionally giving each a little nip on the end. She was now up on her knees and I could see just how wet her pussy was because it was dripping. She had now taken my swollen cock in her hand and was stroking it up and down. With her other hand she began fingering her wet hole. It really trips my trigger when she plays with herself and she knows it. After stroking my shaft for some time she went down on it taking in my whole manhood clear to my balls. With her head now bobbing up and down I could feel my balls stirring and knew it would take long for me to get off. I pulled her head up and said I needed a break. She then moved over onto her back and began playing with her bright red nipples still erect from the clips. I was unable to help myself and went down on her like snow in winter. My mouth had found its way to her moist opening again and I was enjoying just how wet she still was. I began probing her depth with my finger. Pushing up against her g-spot she wiggled her ass in joy. By this time my rod was throbbing. I moved on top and she guided my cock right to her soft wet slit. Kim began to pump me in and out lifting up against me wth her pubic bone until she came again. It was then that she said fuck me in the ass. I was taken by surprise. We had tried anal before but she always said it was too painful. Willing to oblige her I grabbed a tapered dildo and lubed it up. By now she was on her hands and knees awaiting entry. I put some lube on my thumb and gingerly began pushing it in and out of her asshole. After a short time I put the dildo up to her ass and eased it in. At first I thought she was going to tell me to stop but she shyly said just go slow. I obeyed and very slowly plunged the dildo in and out until she was taking the entire length of it. At this point I thought she was going to cum. Her pussy juice was flowing past her lips and was dripping onto the bed. I removed the dildo and positioned myself behind her. I added some more lube and pressed my cock against her asshole. Softly I pushed my cock in until the head passed her rim. Slowly but determined I pushed deeper. Kim let out a moan put her head on a pillow and moved her hips higher. I plunged ever deeper in to her until my balls were hitting her pussy. I could feel her wetness on them. She moved a hand to her now drenched pussy and began rubbing her clit. I continued pumping her from behind while she blindly examined her pussy with her fingers. I couldn’t believe that we had made it this far. My cock is now feeling like a balloon in her tight hole. I could tell that I wasn’t going to last much longer. Pushing back against me with her ass on every thrust I unloaded deep inside her. Continuing to pump her until every last drop had been released. I dismounted her and she informed me that she was not finished. She moved on to her back and grabbed the dildo. By now her asshole had relaxed and she slid the dildo back in where my dick had just left. With one hand pushing the falice in and out she began working her pussy with the other. I watched in enjoyment for a moment and couldn’t resist tasting her just once more. Still plunging the dildo in and out of her ass I sucked her clit until she gushed and my face was drenched. Now both exhausted we laid on the bed and softly touched each other. I let her know just how exciting it was to be able to do something that I never thought was possible for 32 years. Read more »

Part 2: Becoming a Cheating Mistress [MF][D/s][cheating]

If you read part 1, you know that during my quest to become Daddy’s online mistress, I started playing with F.

F is 6 years older than me, tall, slim, dark hair and eyes, very handsome with a long uncut cock. I haven’t mentioned that both daddy and F are European, from different countries, but both with incredibly sexy accents that give me chills and turn me on as I’m a typical American. F and I have always had an easier, more relaxed relationship than Daddy and I. We write when we are free, play when we have a chance, and can go months without talking and still come back to find the other excited and engaged. He likes to be dominant over me, but has no desire to be my owner, nor achingly punish. He doesn’t actively withhold attention or affection like Daddy does. F likes indulging my slutty side and knows how turned on I am when I’m getting his attention. He’s spent hours at work, watching me tease him with my tits out, stripping off my clothes, touching and fingering myself, urging him to join me until he could not longer hold back from taking his cock out in his private office. From what he’s told me, it’s not just my looks that got his attention (he had many admirers on GWA), but the dichotomy of my intelligence against my uninhibited slutty side that makes me irresistible (I’d love to tell you all what I do for work, but I’ve already given too much away). He is willing to share more than daddy, offering his phone number, giving me his full name, letting me know more about his real life; in essence, letting me be his real mistress. And he’s always said he wants to meet me. Read more »

Fun In Colombia [FM]

I recently went to Colombia due to some family stuff that was going on. I ended up staying for a few weeks and while my initial reason for going wasn’t the greatest, I was able to find time to have some fun out there thanks to an old family friend, Carlos, I hadn’t seen since I was 13.

I had already been in Colombia for nearly three weeks and had not gotten to do much other than care for a family member. Her recovery was going well at this point and some more family had flown in to help out and take over. While there isn’t any family my age left in Colombia (all of my cousins now live in the States), Carlos had offered to show me around if I ended up having some free time. Read more »

[FM] Fucked so hard I could barely walk.

I was lost in thought while working out today as I was thinking about the experience I had with a redditor few days ago. I had to finish my workout quickly to touch myself in the shower as thoughts of our encounter left me with more feelings of desire and lust.

It was not my first time with him. Our first encounter was around a week ago after he responded to my dirty r4r for voice chat, propositioning we meet instead. Though I didn’t feel like meeting him at first, I ultimately gave in to his devilish messages. He was persistent and I was totally driven by uncontrollable urges— . After few weeks of traveling abroad and having no sexual contact, I was ready to be wild with someone random and satisfy my sexual appetite.

We had agreed to meet at the bar but the hot and steamy messages got me so aroused that I just invited him straight to my place. I couldn’t wait. We touched, kissed, fucked. He was rough, and I liked it. My memory of how it felt gets my heartbeat racing every time. Just his finger inside my pussy got me squirming and squealing and gave me a mind blowing sensation that kept me wanting more. He fucked me hard and I was completely subdued when he came all over me. He promised another playful fuck-date before the holidays, this is the story of our second encounter: Read more »

My girlfriend tied and teased until shes begging…[FM] Part 1

This will be long…please bear with me – this is my first experience of writing about the sexual exploits of my girlfriend (f28) and me (m29). Im pretty open to sexual exploration. Before we got together we had both been reasonablly vanilla but after being together for a while we have branched out into some bondage/spanking and orgasm denial stuff. Id like to go further and maybe explore threesomes/anal play stuff…but were not there yet.

I dont want to rush this so im going to break it into 2 parts..
I want every experience to be included.

One of our most enjoyable sexual fantasies consists of me being the dominant partner and basically doing what i want with her…basically shes like my sex toy and im allowed to talk to her how i want and explore her body any way i choose. This is my story from last weekend. Im going to call her ‘Em’. Read more »

[MF][old/young] How I started with older men

So after I posted my first anal story (https://www.reddit.com/r/gonewildstories/comments/5iudtk/mf_that_time_an_older_man_introduced_me_to_anal/) I had a few messages asking me how I started with older men. Here’s the story.

I was 18, but only just. I was living with my mother and her long term boyfriend, as had been the case since she split with my father when I was much younger.

My father had died a few weeks earlier and I’d been packing up and cleaning out his things. His friend had offered to help, which was useful – for example, Dad had left me his Triumph motorcycle and I had no idea how to ride it. (I do now!)

So we’re moving some of my Dad’s old things into my place. At the time, and now, I lived in what we in Australia call a “granny flat” in my Mum’s backyard – basically a small cabin type of thing. Read more »