First Time Threesome Sex Stories

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First Time Threesome Sex Stories
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The night where lines were finally crossed.
On Allison’s birthday, she gets to live out her MMF fantasy.
Pillow talk about other man becomes reality.
Flirting leads to an erotic night for hubby and wife.
My girlfriend Sophia pushes the boundaries.
Friends of a friend share their benefits with Will.
Just a short re-cap of my first threesome.
Wife knows his fantasies, wants to make them cum true.
My first threesome, while working as an escort.
Middle aged Asian woman has first MMF experience.
The story of my husband and his first threesome.
Plans for our first threesome hit a critical point.
First time, first threesome on a nude beach!
Anna and I plan for our first threesome with my husband.
My first threesome when I was in college.
A recounting of a life experience, my first MFM 3some.
Christmas shopping with a lesbian friend lead couple to fun.
Sophisticated sexy black woman tells about her first FFM sex.
Our early days and exploration with a panty fetish theme.
Jess returns for a threesome with Aurora and Adrian.
Threesome with an older, wealthy couple.
Mike decides they are ready for a 3rd.
Her first threesome with a man and a woman.
A true story about my first threesome.
A couple bring another man into their bed for the first time.
Claire has her first threesome with Blake and Clive.
A couple shows an old friend the ropes.
My initiation to anal sex and more continues.
The first sexual encounter outside the norm.
Sex in separate rooms turns into a threeway.
A chance encounter leads to an irresistible invitation.
After 16 years, 2 lovers reignite hot passion & add a third.
Wife gives her husband a hot threesome with his cousin.
My wife and I fulfill our fantasy of having another woman.
The first time I shared a girlfriend with another man.
Two men and one woman. Can I handle them?
A woman experiences her threesome fantasy .
I invited my friend over for some fun with my wife.
Debbie is desperate to become a cheerleader.
Sometimes a boy's best friend is his mother's best friend.
She gets it on with Christy & Peter.
My first Ménage à Trois, with friend and stranger.
My roommate's girlfriend includes me.
Ellie's asking price soars after clients rave reviews.
Wife joins me in the men's locker room.
Firearms training leads to much more.
My wife and I invite a friend to join us for sex.
Wife has first threesome around campfire.
Ray meets John and Emily and they click.
David receives the gift of two busty escorts.
He comes home to find his girlfriend with another woman.
Couple get some surprises in their first threesome.
My first education into a threesome.
Young married couple experience their first threesome.
I go to a motel with my boss to meet his friend.
A successful businessman and his introduction to threesomes.
A couple has there first group sex encounter.
Angela introduces Clay to a friend.
Horny teens explore their sexuality and each other.
Couple meets in San Fran for a threesome to be remembered.
Joking suggestion to the boyfriend becomes a reality.
Woman experiencing her first trio encounter.
He surprises her with their fantasy -and she tells about it!
It is hot with me & her & her sister in the front row.
My husband and his best friend please me.
Mom, son and girlfriend have a lovely time.
Two BBW co-workers and I get to know each other better.
Beautiful mature wife has fun with their first threesome.
Couple realise they both share a fantasy for a threesome.
She has many new experiences with young couple.
An unwelcome guest changes his life.
You add another man to fulfill a mutual fantasy.
A first time threesome for a young couple.
Her first threesome, from her husband's perspective.
A story of a woman's first threesome.
Jack's wife surprises him with a birthday he'll never forget.
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Non-porn-performing folks can still have a great time having a threesome. I should know. I did.
Writer focusing on gender, feminism, sex and relationships. Storyteller. Author of the blog: One Year Telling Stories in L.A.
Jul 18, 2014, 03:49 PM EDT | Updated Sep 17, 2014
This post was published on the now-closed HuffPost Contributor platform. Contributors control their own work and posted freely to our site. If you need to flag this entry as abusive, send us an email.
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Writer focusing on gender, feminism, sex and relationships. Storyteller. Author of the blog: One Year Telling Stories in L.A.
"Threesomes are Actually a Terrible Idea" reads the headline of a piece posted not so long ago to The Daily Beast by Aurora Snow , a writer and former adult film actress. Snow's point: If you're not a seasoned porn professional, having sex with two people at the same time can not only prove exhausting, but it may also destroy your relationship. The takeaway? Threesomes are better kept on the brain and out of the bedroom.
I'd prefer to argue that non-porn-performing folks can still have a great time having a threesome.
In my case, my first threesome was with a couple I met while vacationing at Hedonism II in Jamaica. Yes, that's the famed resort dedicated to nudism and swingers. I suppose if you're going to have a threesome anywhere, you might as well have it at Hedonism II.
Why? Because you can be assured that the folks you meet there won't be sexual novices. In other words, it's a good bet they'll already have a couple of ménage à trois under their belts. That means they will have gotten their group sex issues worked out by the time you arrive on the scene.
At least this was the case with Greg and Jess, the couple I hooked up with at Hedonism II. They were certainly sexual adventurers, which was a good thing, because at the time I was going through my own phase of sexual experimentation. I guess you could say that's how I ended up at Hedonism II in the first place.
It's also important to add that Greg and Jess were already involved in an alternative sexual lifestyle, which meant their sexual boundaries were more open than your typical "vanilla" couple. Greg and Jess had a master-slave relationship, Jess being Greg's slave.
But if Greg was Jess's master, he certainly didn't exercise an excessive amount of control over her. The first time I laid eyes on Jess, she was dancing on the floor of the resort disco, sandwiched in between two Jamaican men.
I mean, how many guys would be cool with their girlfriend getting dry-humped by two other dudes?
I can fully understand why these men were attracted to Jess. She was easy on the eyes. At close to six feet tall, Jess was four inches taller than myself. She was thin and blonde and had the face of a model: high-cheekbones and cat-like blue eyes. She wore a red latex dress with a long slit up the leg. Her skin was porcelain white. She certainly hadn't been spending much time on the beach. I don't think getting a tan was why Greg and Jess had traveled to Hedonism II, anyway.
It was Jess who made the first move. While she danced with the two Jamaicans, her head was thrown back, her eyes closed. When she opened her eyes, she and I made eye contact. Soon, she was waltzing over to where I was standing.
She asked me if I wanted to dance. I did. Greg hung back while Jess and I got close. It was Jess who ultimately invited me back to their room. Perhaps I never would have accepted the offer had it not come from Jess.
According to Snow, "The threesome, you see, is something rarely (openly) desired by women."
This obviously wasn't the case with Jess.
I also appreciated that Greg was letting his girl take the lead. It gave me confidence that he wouldn't be overly aggressive in the bedroom.
That's another point Snow makes in her article, lecturing her male readers: "For a threesome to really succeed... you should let your mate pick."
That way, a girl will know the threesome's about her too, not just about her guy trying to use it as an excuse to pick up another lady.
All the rooms at Hedonism II have mirrors over the bed, and Jess and Greg's room was no exception. Once we got to their room, we fell to the bed, kissing, our three tongues entwined. It was an amazing sensation: naughty and gratifying at the same time.
We undressed, then Greg spent some time pleasuring me with his fingers while I explored Jess with my tongue. She was pierced everywhere: nipples, tongue and clit.
Before long, Greg left the bed to sit in a chair just to watch Jess and me together. Greg seemed to intrinsically understand what Snow states in her article: "Guys, did it ever cross your mind that this threesome might not be about you ?"
Our threesome definitely wasn't. I was really into Jess.
It wasn't until Jess and I had been together for some time that Greg went to the bathroom, closing the door behind him. Jess whispered in my ear, "Can Greg have sex with you?"
I also appreciated that she asked my permission first. I'd say that's a good rule if you're going to have a threesome: make sure all participants are on the same page in terms of sexual boundaries. Fingers and oral are the limit for some girls; outright penetration is something else.
I said yes, and as if on cue Greg re-emerged from the bathroom. Little sneak. He had just gone there so Jess could make her query.
Afterward, I left Jess and Greg alone and went back to my own room. I'm not sure what happened once I left, but I doubt that Jess and Greg broke into a jealous argument about the fact he'd finished up with me. I'd also like to imagine that Greg then spent some private time with Jess. Ironically, the whole time Greg and I were together, Jess was telling him, "Baby, I love you."
That also reassured me that I wasn't playing a role in hurting their relationship in any way.
I ran into Jess and Greg again the next evening at dinner. It wasn't awkward when we did. We shared a drink and talked a little, but no one made plans to meet again. We were tired from the night before. Besides, early the next morning, Greg and Jess were flying back to their home in the States.
I can understand why Snow might argue that threesomes can too often get weighted down by petty bickering and bruised egos. Luckily that wasn't my experience. I found two people to have a threesome with who weren't insecure with their relationship.
Snow warns those who want to try threesomes: "The reality is some fantasies are better in your head than in practice."
In my case it was better in practice.
Writer focusing on gender, feminism, sex and relationships. Storyteller. Author of the blog: One Year Telling Stories in L.A.

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I had a very conventional upbringing and introduction to sex with my earliest sexual experience in college with my first serious boyfriend. I only had two more sexual partners before my marriage at 25. My married sex life was also quite conventional, nothing kinky or unusual, but always satisfying for both of us and we raised three healthy, well adjusted kids to adulthood.
I certainly had my share of sexual fantasies like everyone does, but certainly never seriously considered bringing them to life. The possible negative consequences for my personal reputation, job, marriage and family relationships always outweighed any desire to bring any fantasy to reality. But as I got older and children grew up and moved away and I became divorced I realized there were fewer restraints on my personal life, especially with respect to my sex life. But I had no idea how to bring any fantasies to reality, no matter much they fired my imagination.
I had my first threesome when I was 50 years old. I wasn't looking for the experience when it happened but I'm glad it happened the way it did. My husband of 25 years was not involved even though he had expressed interest in trying it several times over the years. The thought of it did not really turn me on at all. His idea of a threesome was another male friend/acquaintance of ours joining us but I couldn't handle the thought of being naked and having sex with another man I had already known for years while my husband watched us.
And having another man watch my husband and I doing it seemed even more weird. How do you face a friend in normal social situations after something like that? Or his wife? No way.
I only ever strayed once during our marriage (another story for another time) though I definitely fantasized about sex with other men regularly and my masturbation fantasies were populated with certain attractive male co-workers or a desirable husband in our social circle. And like all wives I would occasionally fantasize during sex with my husband, imagining that I was being fucked by another man. During those fantasy sessions with my husband, I would always maneuver into a spoon position or 'doggystyle' (I hate that term, btw, but LOVE the position) since it was easier to imagine being fucked by my fantasy lover while being fucked from behind. I would always cum more violently during those sessions, sometimes multiple orgasms, prompting a puzzled response from my husband. I convinced him it was the position, not my active imagination that caused my intense response. From talking with other wives I know I'm not abnormal at all in this way.
I also believe a solid marriage isn't harmed by continuing to practice flirtatious behavior with the right man in the right circumstances. There's no reason to completely abandon those interpersonal skills as long as one avoids crossing certain boundaries. Flirting isn't being a 'cocktease' and it isn't license to sexually grope a woman who you know is married, unless she has already let the man know that's what she wants. Mutual flirtation always gives me an emotional lift and usually leads to good sex later--with my husband, not my flirtatious companion. I noticed that my husband was always a little turned on when he saw someone flirting with me at a social occasion. Probably a connection to his threesome fantasies.
My closest girlfriend for many years, Susan, and her husband Tim had been good friends of ours for years. My husband and I had socialized regularly with her and her husband over the years while they were married and we had kids about the same age. School functions and sports events also brought us into regular contact until our kids were grown and moved away. Sue and Tim divorced several years before my husband and I divorced and I always envied the way she handled it all, maintaining an active social life and always upbeat, not angry or depressed over the split. We no longer socialized as a couple with Sue or Tim, but I still saw her regularly on my own since our friendship was not predicated on either of us being part of a 'couple'.
I got vicarious enjoyment out of our monthly 'Friday night wine tasting' sessions as she related her latest relationship sagas to me. She dated regularly and enjoyed an active sex life, hooking up with the occasional loser but still very much enjoying the good lovers she got to have sex with. Over time I got the sense my husband resented the time I spent with Sue alone, as if she was somehow 'not a good influence' for me, as her 'lifestyle' was unhealthy for her and me. Of course that just caused me to value my time with her all the more.
Sue eventually settled on a long-term relationship with one guy, Ed, a few years younger than her, also divorced who lives in another state. She found that was the ideal situation as she values her 'me time' in her own home and then enjoying his visits all the more when he came to town. I got to meet him several times while visiting Sue for our usual get togethers and always made sure not to stay too late so they could spend as much time in the sack as possible.
He is Definitely a handsome well-built man who works as a carpenter/contractor. Nice biceps and pecs, narrow waist and looks good in tight jeans and tight T-shirt. I instantly added him to my roster of fantasy lovers for masturbation sessions and even during sex with my husband. I never told my husband about the times I spent with Sue while her boyfriend was there as I knew he would consider that crossing a line in some way.
One Friday night a year ago I was visiting Sue and her bf when a sudden blizzard blew in. Her home is in the foothills outside of Denver up a winding highway, treacherous enough in daylight and good weather but downright life-threatening in the dark with ice slicked surfaces and after several glasses of wine. She and Ed insisted I stay overnight in one of the extra bedrooms and I was in no mood to disagree. I called my husband to let him know I'd be home in the morning after the ice and snow had at least partly melted--he was about to call and tell me not to drive home after seeing the weather and hazardous driving warnings on TV, so thankfully no argument over me spending more time with Sue (I didn't mention Ed).
Sue lent me a nightie of hers to wear and I went to bed in what used to be one of her kids' old bedrooms down the hall from the master bedroom. I definitely slept like a log shortly after putting my head on the pillow. Several hours into my sleep I started to have an erotic dream, I can't even remember the details of it but I awoke feeling very wet already. And I immediately heard the stimulus for my la
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