[MM] How I [19M] lost my Anal Virginity to a Man [42M] Over Twice my Age Wearing my Girlfriend’s Clothes

I’ve changed some names and minor details and am using a throwaway to maintain anonymity. Otherwise, this story is 100% true and took place when I was 19.

To begin, I’ve almost always known I was bisexual. I’d experimented with guys in high school and sucked a few dicks. However, I had never gone all the way and actually been fucked. My experimenting with guys came to an end my senior year of high school when I got a girlfriend, and I didn’t have any sexual encounters with another man until my sophomore year of college when this story happens.
My sex life with my girlfriend (19 years old) was great. We ended up going to the same college together, so we saw each other very regularly. However, I always wanted to scratch that itch of losing my anal virginity to a man. So, during a particularly horny moment when gay porn wasn’t cutting it, I made a post on Reddit seeing if someone wanted to meet up. I immediately received a ton of messages, but after chatting with these guys over the course of about a week or so, most of them ended up flaking or being too creepy to actually want to meet up with. I was too nervous to try and hook up with someone from my school, since I didn’t want it to get out to my girlfriend that I was hooking up with other guys.

[M]y Nerdy Girl[F]riend – Things Took a Turn (Part 9 of My Saga with Beth)

It’s taken me a while to get this next part written, in part because these memories were hard for me to relive. I think we all have episodes in our lives we’re not proud of, or that left us with mixed emotions. This was one of those times for me. If you haven’t caught up with the previous account, it’s [here](https://www.reddit.com/r/gonewildstories/comments/y3zgou/my_nerdy_girlfriend_taking_it_to_the_next_level/?utm_source=share&utm_medium=ios_app&utm_name=iossmf). And this is a long story, but if you’ve followed this so far, you’ll appreciate reading the details. This chapter starts off exactly where the last one ended.

—————————————-

“Hey Girlfriend,” I said.

“Hey Boyfriend,” Beth replied. It was the happiest I’d felt in my life, and at that time I thought nothing would ever change that. I was high on the connection we felt with each other. It was new, it was special, it was exciting.

My Excellent Vacation Part 3[Anal][BDSM][BJ][Creampie][Everyone is 18+]

June 22, Morning

I slowly open my eyes and find myself still surrounded by total darkness. Several arms lay across my chest as I lifted myself off the ground. I can hear the distinct sound of several girls yawning while stretching. I feel around on the ground having no idea where my clothes have gone.

“Ah! there we go,” I think to myself, can’t find my underwear, but I can do without them for now. I slip on a shirt, followed by pants, which for some reason don’t seem to fit. Shit, these aren’t mine. I feel around a bit more before giving up having absolutely no idea where my pants have gone off to. I’ll just pull the shirt down just long enough for me to get back to my room. I’ll be fine.

I fold the pants and place them on the ground before feeling around for the curtain. Slightly disoriented, I finally find the curtain and pass through it, pulling the shirt down over my crotch before turning the doorknob. My head pokes through the door. “Okay, the coast is clear”. I proceed through the door and cautiously make my approach to the front desk. “Perfect! There’s no one there this morning.” I pass the desk before hearing, “Cute butt”.

I finally fucked my wife in the ass [Anal Fingering] [Oral] [Anal]

Some of you may remember that my wife (F38) [recently confessed](https://www.reddit.com/r/hotpast/comments/yjmq4p/wife_fucked_her_boss_as_an_intern/) that in her early twenties, she fucked her manager. When she mentioned that her boss fucked her in the ass, this drove me insane: this has been one of my biggest fantasies for years!! I (M41) had never dared to talk about anal to her, thinking she’d find me disgusting. As you can imagine, the thought of my wife’s tight hole stretched by her much older boss turned me on like crazy – especially as I had never done it to her!! I had been wanking imagining her moaning as another man pushed his big cock up her virgin ass, as she lay sleeping in bed beside me.

But the more I was thinking about it those past few days (on the way to work, trying to hide a massive boner in the train; or even at work, jerking off in the jacks), the stronger was the feeling that I should finally open up to her, and see if she was up for it. After all, why would have she told me about it the other day, if she was not open to it? She didn’t say “he fucked my ass, it was awful, I’ll never do it again” either, right? So I planned to leave our three young kids with her parents, and take her out to dinner or something, have a few drinks, and try my luck!

Ass Up in the Air [m29] [f28] [anal] [cons]

**Ass Up in the Air**

By Blue P

**It was the same year as Prince Harry and Meghan’s royal wedding. During the summer of 2018 two young people, worked at the Whippy Dip in Monroeville, Indiana, their hometown. There they fell in love over a shared cup of “Wild Cherry” ice cream while on break. It was sweet, intense, but shorter than either of them wanted it to be.**

Their entire romance lasted only through the summer. Then they were both off to college, and bigger and better things. But today, 8 years later, would be a day of reunion. A time to catch up and maybe even hook up for old times’ sake.

“Chuck? Charlie Culp? Is that you?” asked Kim, in a thrilled and excited voice.

“Kim Seidman?” Chuck responded equally thrilled and surprised. The two spontaneously embraced and kissed on the lips in a moment of unrestrained happiness. Smiling and happy, they were oblivious to the other passengers who were queuing up to board the flight to Denver.

I 32[m] had anal for the first time with my wife 31[f]

So the past year or so my wife and I have been exploring anal. I love to eat, play with her asshole. We got a starter 3 size plug set. I’d use the little and medium size a lot on her. She loves it. She goes crazy when I eat her ass and finger her ass while in doggy.

The other night after a full week of being away and a lot of sexual build up, we had some intimate sex. I had her positioned in doggy and did my normal eatting her ass and fingering her ass. She was extra relaxed with it and loving it. I got the medium size plug and plugged her and fucked in doggy. She told me she wanted bigger. I took out the plug and put a condom on one of our glass dildos and started to place it into her ass. She was going nuts with orgasms. At one point she was begging for my cock to go in her ass. Holy hell I thought! It’s gonna happen!

[F] I (F46) had a secret affair for 8 months. It revitalized my sex life with my husband [PART XII: Stasis]

To start with, I should tell you this is not a sex-heavy post, more of an update on where my adventure of self-discovery has taken me in the last few weeks. Short story long: it’s a bit of a disappointment right now. If you’d rather read about my happier sex stuff, you should start at the beginning of this saga: https://old.reddit.com/r/gonewildstories/comments/u33z2w/f_i_f45_had_a_secret_affair_for_8_months_it/

Anyway, it’s been a while since I posted. No real reason, except that I feel that I’ve kind of exhausted my real life experiences, so there’s not much to say. I’ve tried writing erotic fiction but it feels… unreal. I’ve also tried chatting with other people on reddit, I hoped that having someone to spur me on or help me explore my sexual self would help me scratch that itch, the itch that exploring my affair with Keith helped scratch. But this experience has been discouraging, to be honest. I did have one very hot exchange with a lady that turned into pretty filthy dirty talk–not what I was there to do, but I got into it in a big way. But just that one time. Otherwise, my experience chatting on reddit has been an eye opener, but not really in a good way.

A pet diary – Pet in the wild [f32][f30][M30+][HUML][Sub] – Part 4

True to my conditioning I woke up exactly at 6AM, which
meant that I got almost no sleep at all, but I was trained for that too.
One of the first steps of my routine was full body shaving.
I kept, at all times, my body completely hairless. Although I didn’t need to
touch anything to notice how horny I was, as soon as the razor touched my skin between
my legs I realized that I was out of control, with even the touch of the
sliding blade threaten to push me over the edge.
Working out helped a little bit, even though I couldn’t help
the exciting memories of the gym in The Pod rushing in each time I got in a
machine, but the exercise did help me to distract myself.
I had several chores to run and a Master Nene’s challenge to
complete. I would meet Karl in few hours, which would leave three loads and
three days left. The only problem was that I really wanted to cum, and it didn’t
seem like the occasion would arise soon. Not on its own, maybe I could push it?
“Hey!” I said as Tasha picked up.
“Hi. I didn’t think you’d call so soon.”
“Too soon?”
“No, no.” She chuckled.
“Are you busy today? Can I buy you a coffee?”
Tasha laughed
“I don’t start work till 8, and, after last night I’m pretty
sure I should be the one buying.” She paused for a moment. “Do you mean a coffee
literally or…”
“A coffee,” I replied promptly, “and then some.” We both laughed.
“Do you still want to help me getting off?”
“Sure, of course. But… what about your task?”
“I was thinking, maybe you have a friend who would like to watch,
or whatever?”
Tasha thought for a few seconds.
“Maybe one, yes. I can ask. But you’d still be short one,
wouldn’t you?”
I explained Tasha about my appointment with Karl to sign the
papers in the house and she told me if she could get us the extra person they would
join.
 
 
Karl was waiting by the house’s main door. I couldn’t help
to realize he looked better than the day before and clearly had put some effort
into grooming himself. He was being awkward, not knowing exactly how to deal
with the buyer that yesterday sucked his cock and promised to repeat it today.
I on the other hand, was more concerned about Tasha not being here. I could
clear one more load from my assignment, but I would have to still bear the pain
of my unreleased lust.
“Business first,” I said jovially.
“Of course, of course.” He smiled back. “But for that we
need to go to the notary. I thought maybe you wanted to inspect the house one
last time, you know, make sure the shower is roomy enough.
That made me laugh out loud, both due to his clumsiness and situation
itself.
“I’m sure the shower is roomy enough,” I replied still
smiling. “But now I feel like maybe the kitchen is a bit too narrow.”
He smiled back and unceremoniously dropped his briefcase.
Before he had time to react, I skillfully opened his zipper
and dug his cock out of his underwear. Karl couldn’t stop looking around him,
the unlocked door, the huge windows that spanned the whole room, I could see him
calculating if the kitchen counter covered enough or someone would be able to
see me from outside.
Without hesitation and resigned to another orgasm-less load,
I dropped to my knees and started licking his chubby dick, taking him only few
instants to go full hard.
Karl had to balance himself on the kitchen counter to avoid
falling down when the door of the house opened. He violently pushed my head
away and hurriedly tried, without much success, to put his full erect member
inside his pants.
“Hey Tasha,” I said laughing
Tasha hesitated for few second, frozen in place under the
door frame.
“Sorry I’m late, I guess.”
Karl swung his eyes furiously between Tasha and me.
“It’s ok Karl,” I said. “Come on in and close that door
though.”
Karl was still not having any of it. He hadn’t been able to
mutter a single word, not for lack of trying, but at least he had managed to
somehow pack his dick in his pants, that were now sporting a generous bulge. He
backed out to the corner of the kitchen counter, holding himself against it
with both hands as if his legs were failing him.
As the door closed it pushed in Tasha’s companion, a woman
about twice her size, both height and width, who was very much hesitating and possibly
rethinking about her choices.
“Karl,” I started softly as I slowly stood up. “So, I have
this challenge.” I stopped for a second giving him time to assimilate. “I haven’t
been able to get off for several days, because I can only do it if I’m in the
room with at least another three people.”
Karl’s chest suddenly deflated, as if he just now remembered
he needed to breath.
“We don’t even need to look, if that bothers you,”
interjected Tasha.
Karl slowly regained some color. He cleared his voice.
“You want us to do it with them on the room?” He finally
managed incredulously looking at me.
“That would be wonderful. You think you could do it.”
Now that was a coy way to put it. How many men would admit
not being able to perform, even under demanding circumstances.
“I suppose,” he mumbled.
“I’m willing to help, if you would like that.” Added Tasha
helpfully.
“Me too,” added her companion. “I’m Rita, by the way.”
“So, what’s going to be tiger?” I inquired seductively. “Are
you going to turn down doing it with three women?”
Gradually a smirk started appearing in Karl’s face.
“Well, this is all a bit sudden. But then, all has been
sudden with you since I met you yesterday. Could I interest you ladies in the
master bedroom?”
 
The bed in the bedroom had no sheets on it, only a cover
that probably wasn’t the most hygienic surface in the world. At least it didn’t
look dirty.
“I have only one request,” I interrupted the group as we walked
in. “His load is mine.”
Nods of agreement were followed by mischievous chuckles.
Tasha and Rita grabbed Karl by the shoulders and in perfect synchrony pushed
him on the bed.  Tasha came back to me
and started undressing me, staring me dead in the eyes with a gleeful smile of
lust and desire. Behind her, Rita was doing the same thing with Karl. Once we
were both naked, they proceeded to undress each other and make out standing between
Karl and myself, passionately. Their tongues eagerly fighting, their hands firm
but tenderly running on each other’s skin. From his sitting position on the
edge of the bed, Karl, hard again, was visibly enjoying the show, and the
familiar feeling of goo sliding down my thigh made me realize how much excited
I was as well.
Tasha and Rita took a small break. They whispered at each
other making it impossible to hear what they were saying, only their chuckling noticeable
from where I stood. They then walked to Karl and shared their secret with him.
Obviously, at this point, I was starting to worry a bit about what was about to
happen. There were three people there and all that I needed was the tiniest
amount of action to get me off. Goodness, I would do it myself if I had to so I
could finally relief the pressure that had built up inside me.
“Come,” said Tasha finally. “Elbows on the bed, legs spread,
chin up.”
I obeyed, taken by the sudden commanding attitude. Karl
crawled on the bed clumsily, sitting right in front of my face, his cock erect
a mere inch from my lips. He laid on his back resting his legs between my chest
and my arms. As if rehearsed, both Tasha and Rita arched their legs above him; Rita,
further from me had now his head between his legs, while Tasha was sliding his
cock inside her, so close that her non-existing belly rubbed on my face.
Rita shook her hips, in circles first, then backward and
forward. I couldn’t see Karl’s tongue, but I had a pretty good idea on where it
was. Tasha, on the other side, was moving up and down with great ease, changing
speed from real slow, to very fast, to something in between, taking with ease
all of Karl’s member inside. All I could feel at the time was some heats of her
belly on my face, a quiet jiggle on my boobs and an ever increasing-tickle
caused by my excitement drooling down my legs.
After a few seconds, Tasha’s hands were caressing my bald
skull, only increasing my frustration until she decided I could help, and
gently pushed my face onto Karl’s crotch. Before I knew it I found his balls in
my mouth as Tasha’s cunt slid up and down my scalp.
Rita didn’t last long before her moans clearly announced her
orgasm. If that wasn’t clue enough, she stopped riding Karl’s face immediately
after, only to jump on my back, riding me like a horse and almost making me
lose my balance. I don’t know if I was more surprised for what she was doing
per se, or the fact that she just met me and had no second thoughts about doing
it. When she started slapping my butt, hard, as spurring a mule.
Tasha then started the, already well known to me, chain
reaction of breaths and moans as she climaxed. At this point, my face was a gooey
mess and I my chances or getting off slowly evaporating.
Tasha moved away and Karl didn’t miss a heartbeat to fill my
mouth with his cock. He just pointed it to my open lips and before I could
react a hand pushed my head against it with violence, so much so that, for all
my training, I actually had to resist my gag reflex.
Resigned to only getting one load off of my assignment from
this interaction, missing the opportunity to finally getting off, I started
working his shaft, as energetically as I could to be done with the whole thing.
It didn’t take long, and in few seconds both Rita and Karl pushed my head
against his crotch as he flooded my throat with his seed.
But as luck would have it, Tasha and Rita weren’t done. As
Karl moved away, Rita slid in, same position and wearing a strap-on dildo.
“Is not as cool as yours, but I think it will do,” she chuckled
as she started fucking my mouth with it.
Rita had moved away, and I appreciated the respite while I
continued working on the silicone toy tirelessly until Rita decided it was
enough and pushed me back to make me stand. She moved to the edge of the bed
and made me turn around, and holding me by the hips she pushed me down until
the dildo entered my ass. I had freedom to move now, so with a few adjustments
I was able to take the whole thing in. Anal only would rarely bring me over the
edge, but in this occasion it would, I needed only a few more seconds but I
didn’t want to wait, so I reached to finish the job with my own hands.
Tasha obviously noticed, and obviously disagreed, for as
soon as my arms reached forward she grabbed them and pull them back. Now, not
only could I not touch myself, I also didn’t have the proper position to move
harder. Rita then appeared in front of me, and yes, she was wearing another
strap-on. More carefully than she need to, she entered my pussy and coordinated
swings with Rita for the double penetration. This would last seconds, I knew.
But there was one more surprise; Karl climbed the bed on his
feet and walked toward me. Hard again and full of lust he didn’t lose time and
filled my mouth, still sticky from his previous go, holding me by the back of
my head and fucking it mercilessly. I could go anytime, I was there. I had been
ready for so long I would just let go. But I was competitive and proud now, so
I took the opportunity to show off once more. With all the focus I could muster,
I held my orgasm until once more Karl came into my throat, lighter now, more
liquid but with more pressure than before. My body shook as I finally allowed
myself to let go, shivering radiating from my crotch in waves of unbearable
pleasure, not able to scream, barely able to breath, my arms succumbed and I
fell back, Tasha’s breast cushioning the fall, Karl’s dick left behind. Similarly,
with the inertia Rita’s dildo popped out and a gush of juices was ejected from
my body.

[C] Tiffany’s New Life As A Cumslut [Part 1] [Rape] [Gang Rape] [Branding] [Internal Urination] [Prostitution] [Mind Break] [18+ All Characters]

[Features: Rape, gangrape, branding, suffering, yuri, sexual racism, BBC gang, internal urination. This is a harder one.]

It was a dark and dreary night and down a cold path a woman walked. The city was nearly dead silent at this time and it was doing nothing to help Tiffany’s nerves. She was alone and walking quickly. The day had started out so well and then gone nearly immediately to shit. She had been contacted by a modeling agency after seeing a few pictures of her online. She’d done her due diligence and checked around online, making sure they were legitimate and found out they weren’t just known, but well known. Doing everything from magazines, to calendars, to commercials. She’s been more than happy to go. After all, she didn’t look bad.

Standing at around 5’7, she was a beautiful Asian woman. Long black hair, perky breasts, perky ass, thick thighs, and even a cute face, she knew she was a whole four course meal. The idea of seeing herself on a billboard made her heart spike.

So of course it hadn’t happened.

I’m an Addict

His hands were hot like a black flame candle. A slight spark at the tips of his fingers every time he touched me. That “tingle” when he touched me is what drew me in. It was like that first bump of cocaine you do at some bonfire in RURAL upstate New York in the summer with all your older brothers friends at 16 (IYKYK). And just as addictive too. Man I would do any fucking thing for that touch…again and again…

But fuck…his hands really were just the start…

The things this man makes me feel when he is inside of me…LADIES! Listen up! Hear me LOUD and CLEAR! Go out there and find you a Capricorn Man. And dudes…you hear this too (because I know y’all are reading). Let me just…his dick…it is like THE perfect size. The perfect shape. The way he moves his big black dick so deep inside of my squirting (YES I said SQUIRTING) incredibly soft and plump white pussy…He really is a gift to the world…