[Humil][chastity] Innocent naive college virgin wins a sorority’s life time virgin award. His prize isn’t what he thought it was.

I was homeschooled by my overbearing mom until college. She wasn’t religious, but she was as sheltered and naive to the world as one could get. It was never something I thought about growing up, just as a boy doesn’t know what something is, like a combustion engine, until he’s told of its existence, I didn’t know about sex. I was aware people had it, it’s how babies were made, but outside of that, I was clueless. I never thought it’d be a prominent factor in my life. Boy was I wrong.

I started college at one of the largest universities in the country. Unbeknownst to me, also the largest party school. I found this out via a sorority event believe it or not.

At the time I was unaware, but apparently during pledge week for the major sorority, the pledges are given the task of finding a virgin and bringing them to a party. Like a dinner for schmucks type situation.

Deus ex Machina [MF]

This happened 7 years ago. I was in deep depression before it happened. My wife left me. My PhD research was going nowhere, stuck in the same place for years. No plan B. Nothing to live for. Not good.

My escape was going into online anonymous chat rooms and chatting up girls. On rare occasions, they were actually girls. On rarer occasions, I got to meet up and hook up. Even got some FWBs. Setting my standards very low helped. My only rule was unmarried and has a uterus. My other only rule was no falling in love and no getting into serious relationships.

One fateful night, I met a girl there. I thought she could be the one – the elusive hookup after just one convo. But she turned on me in the last minute and said she wanted more than one night. So one conversation turned into two, which turned into two months of online chatting, every night, all night.

Boxes Part 1 [bdsm] [MMFF] [Fsub] [Mdom] [voy]

She looked around the room again and took in the scene. People bustling around her, snippets of piped in jazz, waiters and waitresses navigating the crowded tables, drinks piled precariously high on silver platters. Suits and sparkling dresses. She adjusted her own dress. The fit was right, which had been a surprise to her, but she was not used to the cut: hem resting just above the knee, black chiffon obscuring the plunging neckline. She felt exposed, as if everyone in the room was looking at her. And they all knew why she was there.

A box had come with the dress. The box contained a tag and a card. The tag was a simple piece of copper, not much bigger than a coin. On it was engraved her name. Her new name. The one that she had been given by him. The one she had earned after he had tested her to see whether she was worth naming. She had done everything he asked, until she was gasping for air, until her face was burning, until the tears streamed freely down her cheeks. Until she ached to be filled, pleaded to be hurt. Until the lack of release made her half-mad.

First time at a nude beach [MF], [voyeur], [nude beach]

This is 100% true. It happened in August of 2016 in Austin Texas (Hippy Hollow). Feel free to message me with questions. I’m the male side of the relationship. This is pretty long. My first story on reddit. I have many more true stories, and hope to create many more with my wife (and others). I wrote this last year right after it happened. Enjoy.

[M]Pegged for the [F]irst Time!

My wife pegged me last weekend and it was unbelievable. Let me start by saying that both of us are bi, but enjoy playing with other women the most. We went to a wedding that was only about ten minutes from our home so it was a quick ride home from Uber. The reception was a lot of fun and we both had plenty to drink. We enjoyed the fun and as we usually do, started looking at the other people at the reception that we found hot. This is always fun and gets both of us pretty worked up, especially with some alcohol on board.
There were plenty of both hot guys and hot girls and we picked a few that we would both have liked to take home but our sex life is kept discreet from our friends and neighbors so we really couldn’t pursue any of this tonight. We got home about 11:30 and while I took care of letting the dogs out, my wife went upstairs.
Dogs taken care of, I headed upstairs and opened the bedroom door to see my wife lying on the bed in a sexy light purple bra and crotchless panties. She looked amazing and next to her on the bed were our two boxes of toys. We had amassed a pretty good collection of all different kinds of vibrators, dildos, and other toys including a strap on that we had talked about but never used.
We started kissing and my fingers found her pussy as her hand found my cock. She was already wet and I couldn’t wait to taste her. I began eating her pussy as she moaned and slowly moved her hips. I sat up and grabbed her legs rolling her to her stomach. Immediately, I began to rub her pussy from behind and spread her legs. She pulled her knees up raising her ass into the air. I spread her cheeks exposing a gorgeous ass hole that I couldn’t wait to get to. I took my already wet fingers and slowly circled her ass putting a little more pressure each time until my finger was easily sliding into her ass. I reached into the toys and grabbed a heavy metal butt plug. My tongue danced across her ass as I lubed her with my saliva. She could see me behind her as I put the plug in my mouth and covered it with spit and warmed the metal. From my mouth the tip started to push on her ass as it slowly slid deeper in until the base rested between her cheeks. I now my wife loves the feeling of being full with a plug and she was surely showing it.
Know it was my turn. She took my cock into her mouth for a few seconds before she told me to get on my hands and knees. She got behind me and I could feel her tongue on my ass while she reached between my legs and grabbed my balls and cock. She continued to eat my ass for a little bit and then she grabbed a dildo and started to rub the head against my ass. She could tell by the noises I was making that it was really turning me on. Then she asked me……”Do you want me to fuck you in the ass?” And of course my reply…”yes.”
We got the harness and dildo and she put it on. It was incredibly hot to see her there naked except for the strap on. I really had no idea what to expect when she looked at me and said “ I want to see you suck this dildo like a cock”. She pushed my head towards it as I opened my mouth and began to suck on it. She knows that I have had sex with other guys but it was before we met and she has never seen it. She started moving her hips as she pushed her “cock” deeper into my mouth. She was obviously turned on by this and so was I. After a few seconds she pulled away and told me to turn around. I got back on my knees with my as in the air as she dripped lube onto it. I felt her fingers making circles around my ass she then slid her finger deep inside me.
She took her finger out and I felt the tip of the dildo on my ass. She asked if I was ok and I replied yes. Slowly she started easing the tip in and I felt my ass start to stretch. There was discomfort but not pain as the dildo went deeper into my ass. Before long I felt he r hips against my ass as the entire length was deep inside me. It felt great and was getting even better as I relaxed more and more. She began to thrust slowly at first then harder and at one point reached around to grab my rock hard cock. It went on for a couple of minutes that felt incredible. I was getting closer to cumming but still wanted to fuck her some before I did. She took the dildo out and I turned around to go back down on her. I slid the harness to the side and buried my tongue into her pussy. It was the wettest that I have ever experienced with her. She was close to having an orgasm and I kept going until she just exploded in pleasure.
I wanted to be inside of her so bad and she knew it. Off came the strap on and she said “I want you in my ass” and climbed on top of me. I reached between her legs and slid my fingers between the base of the plug and her flesh. I slowly pulled the plug from her ass as she moved to guide my cock in. She was already relaxed as my cock slid into her ass. I felt the tightness as she rode up and down while I fucked her. Before long I could feel the cum building as she moved to keep my cock as deep as possible while it pulsed and filled her ass with cum.
She could tell I was done and just sat there for a bit. It still felt incredible but so sensitive. She got up and spun around placing her pussy in my face. The cum ran from her ass and started down to her pussy as I used my tongue to clean her up and the mixture of my cum and her juices. Finished we both lay next to each other and just enjoyed the moment.
We got into the shower to clean up, washed the toys, and got back into bed for one of the best nights sleep ever. The next morning we talked about everything that happened and neither of us had any regrets. We both agreed that we were going to expand our sex life even more with my wife saying she thinks she wants to see me suck a real cock.

Horny couple wants a younger man to join them [MMF]

*Names of people and places have been modified a bit for this story*

I’m a single guy, late 20s and I live in the NY area… I’ve always been really turned on by the idea of sex with an older couple. I’m bi and have wanted to be with a more mature man and woman at the same time. So, start a few months ago I began looking around online for a couple who wants to have a threesome. Maybe 3 weeks ago I found a posting on Craigslist “casual encounters” that said “Long Island couple seeks third for bi threesome”. I’d responded to a few of these already (with no success) but this posting seemed a bit more human and real. This couple was looking for someone to fuck both of them in the ass! Unusual request (at least in my brief experience looking) but I am open to that, so I answer the ad.

A few hours later a woman emails me back and wants to chat over text. I’m initially very skeptical (why not use CL email relay?) but after a few back and forths I give my phone number and we start texting.

When she took my ass [MF] [pegging]

She knelt on the bed between my legs looking down at me, rubbing lube all over the large silicon strap on she was wearing. Finally my wife had consented to peg me, and I could tell that now we were about to do it she was excited about something so dominant. She was enjoying seeing me tied up in nothing but a skimpy man thong that she had picked out for me. Seeing her naked body wearing the purple cock had my 8″ cock pressed against the soft fabric so hard it hurt.
After finishing lubing up the big toy, she put some more lube onto her hands and be can to work it onto my hole while she leaned forward and began licking and biting my nipples. She was so perfectly positioned that her perfect d cup breasts were rubbing against my now throbbing tool. I let out a soft moan of pleasure and she paused to say “tell me what you want baby.”
“Fuck my ass” I said as I looked into here eyes.
Slowly she positioned herself so that the tip of the toy was pressed against my ass. Then she pushed and my eager hole accepted the huge rod inch by glorious inch. Once she was buried in my ass she began making slow short thrusts, waiting for my hole to get used to the size of the toy. As my ass lossesned around the toy the thrusts became longer and more deliberate until she was truly pounding me.
“Mmmmm your a dirty bitch'” she whispered in my ear as she pounded away. My only response was to moan louder.
Then I felt one of her hands move to my throat. I groaned again as she began to choke me hard, only pausing to smack my face and call me her bitch again. Occasionally her other hand would reach down and pinch one of my nipples hard, or grab my hair and pull my head back so she increase the choking pressure.
After a while she pulled out and said “put your feet in the air bitch!”
I gladly obliged and she moved back into position with my legs over her shoulders. When she thrust her fake cock into me again I realized that this position had an unexpected advantage, my cock was now poking between her large perky tits and she pounded away at my ass. Almost immediately I felt my balls begin to tighten.
“Baby I’m going to cum” I shouted.
“Do it, you little bitch. Cum for me.” She replied and began to thrust harder and faster my cock still between her tits.
I felt the orgasm rock me as I yelled out in pleasure. As my ass clenched around the dildo, cum exploded out of my cock, covering my wife’s tits and even shooting onto my face. As she pulled the strap on from my ass, she moved forward and licked the cum from my face. Then she stuck her cum covered tits in my face and said clean them for me, and I licked all of my juice off.
I spent the next half hour going down on her until my face was covered in her juices.
We haven’t had an opportunity to try pegging again, but you can bet that I’m waiting very excitedly.

Return to the swingers club, first time not for work [Group] [Long]

As last time I hope my English and writing isn’t too bad. I am neither a practiced writer, nor is English my language. After I posted my [last and first story](https://www.reddit.com/r/gonewildstories/comments/6yxxy9/my_bosses_swinger_wife_mf/) someone in the comments said, they’d like to hear more if i had more stories.

After the encounter with my bosses wife, Mary, I didn’t go back to the swinger club in a private capacity at first. I worked there a couple of times, whenever my boss needed an extra security/ bouncer present. As much as I wanted to go back, the thought of having to kick out or to restrain people or their partners I have had sexual relation with, kept me from doing it. Plus I was busy with my job and studies at university.

It was a few months later, that I got a new girlfriend, Lisa, another student from my university. I had hidden the fact I worked at a strip club and some times at a swingers club. As I thought it would needlessly drive her away. After a while though she found out, and was less pissed about my workplaces as about me lying. In fact she surprisingly interested in the swingers club. Ashe kept asking me things about it. As I later found out her parents were active in the lifestyle, but it wasn’t a topic one would necessarily want to broach with one’s parents.

[MF] Last night I met a couple at a bar… [xpost r/stupidslutsclub]

After an hour of drinking, flirting, touching and kissing, I went to a hotel with the husband and sent his wife to my husband at home.

Met them online and spent about a week flirting over Kik. Decided to meet up with them at the bar close to my house while my husband was at home. Wasn’t sure if it would go well so I didn’t tell him what I was up too, he just thought I was meeting a friend for a drink. (This stuff is all agreed upon, btw) They were a little older but both of them were fucking sexy, and the wife was a goddamn cougar… She was all over me from the get go. She just oozed seduction, I knew my husband was gonna have a blast with her. I’m not really even bi but I’d be lying if I said she wasn’t turning me on.

Request: Erotic stories for a specific fetish of mine

Stories similar to these.

https://www.literotica.com/s/just-a-feel-ch-02
https://www.literotica.com/s/beware-mr-green

Basically a dirty old man (genuinely dirty, filthy fat and balding) scoring a hot girl or woman who is disgusted by him at first. Bonus points if he cucks a handsome guy and impregnates his wife. Also no one should be black. She should be indifferent to him or disgusted by him at first. The POV should not be from the old man or the woman’s. Either the author or the cuck husband.

I’ve read most of it in literotica or anything available on asstr.