In Her Arms [Requested][MF]

As requested by /u/throw_away_my_life_
***
“Hey sweetie, how was work?” Jane gave Tim a hug as he walked into the living room.

“It was alright,” said Tim. He nuzzled his head against her, taking in her scent. Tim didn’t mind that his girlfriend was taller than him— he liked the safety and comfort.

“You okay with some leftover pizza?” Jane asked.

“You know I love pizza.”

“Yea, I do.” Jane smiled and pecked him on the cheeks. She got up and headed into the kitchen, grabbing cold pizza from the fridge. Tim heard the click of the oven turn on.

“You know you could just microwave them, right?”

“What am I, a monster?” Jane yelled from the kitchen.
***
Tim smirked silently in response, and went back to his phone. The two laid in bed together. Jane sat up against the wall reading her kindle, while Tim lay on her lap, looking at his phone. Every so often, Jane would absentmindedly run her fingers through his hair. This was their nightly ritual.

“Heh, says here masturbation reduces the risk of prostate cancer in men,” Tim read the article out for her.

How I ended up having anal sex with a girl before PIV (Interracial, Virgins, Long) [m18/f18]

So some disclaimers: this is long and will take a while to get to the sexual stuff. I have changed some superficial details and names to protect identities but otherwise this is a completely true story of my first sexual experiences and how I ended up having anal sex with a girl before I’d had PIV sex. I am not a writer of any description and this is my first attempt at a story so be gentle. Also, be assured that there is no Loch Ness Monster. Look for the break if you want to skip to where things get sexual.

I left high school a virgin. Not just a virgin, but a never been kissed virgin. Girls wouldn’t just turn me down, they seemed to be a bit insulted that I thought I had a chance. I was short, pale, and geeky. I had acne, braces and was painfully shy. I went off to University aged 18 with my acne gone and braces removed. Regardless, I had built up a lot of insecurities about my attractiveness. Girls didn’t seem to be horrified by me anymore but I was still no girl’s fantasy. A solid 5 out of 10. But that was ok, I had long since made peace with the fact that I was no model. My confidence slowly grew from nothing to still almost non-existent but something. I went on a few casual dates and even kissed a couple of girls, but never got any further than that.

[M]y first MFM Last Night With My [F]riend And Best Guy Friend [M](31, 39, 26 respectively) [Anal] [Squirting]

I’ve been a long time lurker in this sub, and had always hoped to have a story worth sharing. Last night, it finally happened. Skip to the break for the sexy times.

The background:
My best friend Nate and I, 26 and 31, have been always on the verge of arranging a three way, with someone always backing out at the last minute. He is 6’2 and 210 pounds and I am 5’11 and 205 pounds. After years of this I assumed it would never happen. Last night however, our mutual friend Erin messaged Nate out of the blue looking for some dick. Now, I’ve known Erin for the better part of 8 years, and always found her attractive. 5’7″, 140 lbs, curvy with an ass that looks great in anything, small B cup tits that survived 3 kids and perfect pointy dark nipples that love to be sucked and bit. She rocks a short pixie hair cut and just looks great for someone nearing 40.

So. She was looking for dick. He and I were hanging out, and of course always had this threesome in the back of our heads so Nate texts her: I’ve got a cock for you, but tonight I want to do something adventurous, maybe a threeway, are you down?

[Touch, Kiss, Oral]How I Became A GayBro (MM)

I guess, like most bros, my story starts in my youth. Regular stuff you know. In middle school and jr. High (5-8 grades). I would go to my friends house where he had found his dad’s old porn mag stash. We would sit in his room or go out to the barn at the back of the pasture and look at all the topless chicks. Sometimes we would JO, sometimes mutual JO, and there were even a few BJs in there.

Looking back it is quite hilarious because, especially in the early years, because we didn’t actually know what we were doing so we would just do stuff till we got tired. It wasn’t until 7-8 grade that we realised that there was a completion state. After 8th grade me and my friend kind of drifted. We went to high school and kinda found our own groups.

I never really struggled with my sexuality, from a pretty early age despite my homophobic family I was pretty aware that people are people. I have always assumed everyone is bisexual/pansexual and if you see someone you like, start a conversation. People will catch that you are trying to flirt and if you are the wrong gender for them they will most likely let you know. I don’t understand why that is such a difficult concept to understand. Anyway, I digress.

M/F/F (M)y first time threesome with my girl(ff)riend and her classmate, with some pegging.

Earlier this week my girl friend finished her last semester in grad school and decided to have a party for some of the girls in her cohort. Because it was all women, my girl friend asked if I could entertain myself or go someplace so they could “openly share memories and stories.” No biggy, playoff hockey and basketball with an open excuse to drink, done. I spent a few hours at the bar near my house and came home around 11pm and only one car was remaining in the driveway. I casually walked through the door to find my girlfriend and one of her classmates, Carol, laughing and giggling on the sofa. Carol is 26 about 5’5″ with shoulder length dyed blonde hair with brown roots, she has a thin frame with small A breasts and no ass and looks very younger. Emily, my girl friend is 5’1″ with long wavy hair brown hair, she is curvy with almost DD breasts. I am 5’8″ with a beer belly that formed after college, and still going on see above, but not awfully big. My dick is right around average at just under 6″ but I like to say 6″ to feel good. Back to the story.

Answered a craigslist ad from a guy willing to suck off straight guys, got more than I bargained for [M/M]

I should preface this story by saying that I am straight, generally, and had never been with a guy before this story. This was a few years ago, when I was 24, living in New York City and dating a girl long-distance.

My girlfriend and I had been together for a few years, since college, but an amazing opportunity took her to another city for two years. I found myself on the Greyhound a lot and, when I wasn’t with her, often sexually frustrated–especially as I saw all my friends living it up as single guys in their twenties in NYC.

One day, on one of those nights when I was away from my girlfriend all my friends were out hooking up, I strayed from my normal porn appetite onto Craigslist’s casual encounters page. I wasn’t really planning to do anything there–I had never cheated on her–but I decided to browse and click a few ads. I started on the w4m section, but it soon became exceedingly clear that every one of the ads there was posted by a prostitute or a spammer. So I drifted over to the m4m section, mostly out of curiosity–and while most of the ads were not my style, one caught my eye. It was a guy a little older, 28 years old, who had posted a simple message offering a free, no-strings-attached blowjob to a straight/curious guy. His apartment would be dimmed with straight porn on the TV, and whoever answered the ad could walk in, get sucked off, and leave anonymously.

The best sex is unexpected

At my probation group therapy, for bad kids like me, was a girl every kid there eye fucked, while sharing with the group how many months they were sober. She was a ten, thin, short, a nice round ass, tiny stomach and big perky tits she always showed off a little. The counselor mentioned the day she joined the group how she looked just like a young Megan Fox, and she did. I laughed, and told the group that Megan Fox was damn sexy. She blushed and smiled at me. I couldn’t believe I might have a chance. While we were sitting in group, I spent my time undressing her with my eyes, picturing how I would please her. She started to notice, and I was shocked and she teased me, spreading her legs a little, hiking up her skirt, or sliding her hand under her waste band. She even dropped a paper and bent over, giving me a view of her tits popping out of her bra.

Cum makes the best lube [M21/F20/M21]

Like my other stories, this one is 100% true. This is another threesome story from an ongoing sexual relationship my girlfriend, a close friend of mine and I had for a few months while in college, for more background, see the previous stories below, however essentially the back story is that my friend ended a long term relationship and my girlfriend offered take care of his physical needs for a while until he was ready to start dating again. Over a period of several months my girlfriend would frequently meet up with my friend and either jack him off or blow him, occasionally though, we would have a threesome together.

Previous stories are here:
https://www.reddit.com/r/gonewildstories/comments/4ad4ap/first_threesome_with_girlfriend_and_friend_mfm/

https://www.reddit.com/r/gonewildstories/comments/4ahv5y/minibukkake_with_girlfriend_and_friend_mfm/

https://www.reddit.com/r/gonewildstories/comments/4amy7i/threesome_on_the_beach_m21f20m20/

https://www.reddit.com/r/gonewildstories/comments/4bfhaw/fourth_threesome_got_more_adventurous/

First time with a shemale

she-male experience
I have alway had a fantasy with being with a she male for years I find them beautiful , exotic and until recently I found out its something straight men are naturally attracted due to them being so fem. Its the fact there are woman with penis with is the holy grail.
One day I am looking at she porn at shamble gods.com and I decided to look on craigslist and just look if there any in my area. I find one and answer to an add to a woman called she-male jem, she is looking for a bottom boy for the night. I send her a pic and responds to me back with her number and we talk for a little about what we want to do. This is a pic of what she looks likehttp://img.adultsearch.com/classifieds/798345_0uiaw18lT0oOKudJtFT.jpg and this is a pic of her cock http://img.adultsearch.com/classifieds/798345_74OFetCTBEJlzYLz2CtU.jpg
it looks nice and big and like the previous story that I want a prostate orgasm and experience a beautiful woman with a cock =). She instructs me to go buy condoms and she has lube. So on my way to go see her I stop at a gas station again but this time a chicken out because I didn’t want to be judged buying condoms. =(
Once I arrive it looks like a really bad area and i start to get scared. I was about to leave but she came out greeted me while I am in my car and told me to come and fallow her into her apartment. Her apartment is really small and by the looks of it she lives by her self. I laugh a bit because there is porn on when I enter the living room and we talk about ps3 and how she knows how to fix them.
When I first saw her with my eyes I realized she is really tall and she is beautiful and the pics she sent me do no justice, she looked way better in person and even better than her porn videos. We talked and she told me, she was a porn star for a while for she-male strokers and she told me stories how men with there wives would recognize her at the stores.
After a while she asks me what turns me on?
I reply “I love thongs”! like from my first experience with popping my cherry I lost control of my self when I saw the skater girl in just a thong.
She tells me is a sarcastic way “I am not wearing any underwear” and I look down and she was just wearing a skirt and I see her beautiful cock hard and it puts my 5 and half cock to shame. it looks huge and tasty and warm.
I am dumbfounded and with my jaw open I ask her if I can suck on it and she replies “yes with a giggle”. Know this is my very first time sucking on a cock at all and especially at this size its huge. I lick the head gently like ice cream hoping to get that cream filling at the center.
Then I finally put it in my mouth and I am moaning with so much excitement. I am kissing her cock, smelling it, rubbing it and trying to take as much as I can in my mouth. I can tell she is getting really Horney.
She asks me did you bring the condoms? I reply no because I become scared and she looks at me, with so much disappointment. she just tells me to keep sucking and finally I pull my pants down and I grab our cocks together like I am stroking just my own up and down together. it really feels nice to rub a cock on another cock.
She asks me “is there anything you want to do?” I reply I have always wanted to 69 and we do just that. With me on bottom of course =) and her cock and ass in such perfect view I start sucking and at the same time she is sucking me good. like omg !!!!
Then finally I hear her say “screw it I can’t take it anymore” and puts me an my all fours on the coach and asks me if I have ever had sex with a guy before and I lied and said no ,because The other story with the guy.
She puts lube on her finger and goes in me it felt so good entering my tight little boy pussy and then puts some lube on her cock before entering me. Now this cock was way better than that guys cock before. I felt so much and she was way better in every way. She tells me that I am so tight =). She is really making my ass stretch to its limits. After going in slowly she finally all the way in me. Then here comes the best anal sex I have ever had in my life.
She pounds me at a long slow pace at first it feels so good I can feel it through my whole body. my ass is being dominated by the hung shemale and I love it so much. and at the same time she reaches for my cocks and is jerking me off with her in my boy pussy taking in her cock.
It gets bad to the point I am moaning so loud I wonder if the next room hears me getting fucked by this beautiful woman. She is sending me shockwaves through my body aching for my prostate fun.After a while she asks me where does she wants me to cum? I tell her to cum in me because I want to feel her load in me and wanted to see how it felt. Her cock starts to throb in contractions and She cums right in me with her perfect load in me and my ass is eating every last drop. She is moaning in excitement and her cock is drained from my ass =)
Next she tells me its my turn and I tell her I have never gave anyone anal before and she smiles and says “nice this is going to be your first time.”
She tells me sit on the coach and I do so and she is standing over me with her ass at my face level and slowly puts her ass hole right on my cock. She starts to put her body weight on my cock. She starts and slow adjusting her pro ass on my cock then She is bouncing my cock and I feel the warmness tingles sensation of me cumin and I ask her the same question right before I let go of my seed “where do you want me to cum” and “she replies in my ass and I my cock shoots my load up her dominate ass. =)
When she gets off my lap my dick pulls out with such force it hurts and she giggles. At this point my cock is to senstive.
When I am leaving she is naked telling me goodbye with her door wide open and she told me “you are going to see me again”. =) Which I still crave that dick sadly. And before I leave I hug her naked body next to my own with clothes and tell her goodbye and I secretly wanted to suck her goodbye and taste my own ass of her cock. but I left to crave her cock once again.
I went to sleep with cum in my ass dripping till morning and I loved it. =) Yes I do love shemale and still want to get dominated by a strap on.

In the middle [Bi] [FMM] [Anal] [Reluc] [Fdom] [Msub] [Mdom] [first person]

I’m in a room, I don’t know where it is, could be a hotel, could be somebody’s house, all I know is that it isn’t my place. There’s a bed against one wall and an armchair facing it but there’s also a mat on the floor and I realise that the room is very much used for one thing only, and that thing isn’t sleeping. The door opens behind me but I’m not allowed to turn to see who it is because She’d punish me if I did.Her voice both puts me at ease and inspires fear in me simultaneously.

“Jazz, I’m glad you’re more with it now. I’ve brought a friend here to help me to teach you a lesson because you’re such a quick study.” Her hands run between my legs from behind as I remain as still as possible on all fours. My cock starts to stiffen due to a combination of the tone of her voice and her touch and it’s then that I feel her slip something over the head and fasten it behind my balls. She obviously needs me hard for something. She walks into view and I see another pair of legs beside hers they could be anybody’s legs, but I know they’re not female from the way he stands.