How did your first threesome eventuate and is there anything you would have done differently to enhance the experience? The same question for hotwifey

[MakeMeWetAF]

So, my first was… interesting.
I was 19. I think I’ll answer the question about what I would’ve done differently first. Then I’ll tell you the story… (It seems that you like the story part, a lot)
The main thing I would’ve done – and this perspective was really only available to me in hindsight – would be to have paid equal attention to both of the women.
One of the women involved was an ex-girlfriend who was still very much in love with me, though I not so much with her. The friend that she brought along was someone that I had secretly begun seeing several months beforehand. And, she was the epitome of sexual perfection for me. We couldn’t get enough of each other. Thus, the night ended in disaster. No exaggeration.

Oh gosh! Now why do I get the sneaking suspicion you've reeeally saved the best until last with this first threesome foray as a horny 19y/o male...This blasted School of Life can be so very brutal at times! Thankyou so much for sharing these vital lessons here.

So with this first installment, I can see that you "miiiight"...have dropped the ball (I mean...BOMB!)in ensuring EVERYONE had a good time by "kiiiind of leaving" the Ex out in the cold... all alone...like the Lone Ranger...longing to devour the fruit of your loins...while you and your new love interest were lost in eachother's eyes, arms and nether regions........ The benefit of hindsight would have definitely been handy to have at the time.

Shit, Man...!!! I'm almost too scared to read the next installment however, it seems that you're still alive and in tact... so that's a positive Ok, deep breaths, I'm bracing myself and about to dive into your next chapter with this....

 

[MakeMeWetAF]

But, here was the event in question:
I was 19, like I said, and I was only recently out of the Canadian military. I had started modelling just a few months beforehand.
One of the largest agencies in North America at the time – John Casablanca’s – had put on a major male modelling competition – Discovery ‘83. Apparently 5000 men across North America – but mostly from Canada, from what I could tell – had entered. They whittled that down to, if memory serves, 13 of us.
Despite my lack of experience, I had managed to place second, with the winner being a slightly older, much more experienced guy who was represented by Casablanca’s (go figure).
Either way, it was a huge deal for me…
And, it was a huge deal for my ex who was my loudest supporter that night in the theatre. She had brought her/our friend Linda along to support me.
But, I ended up going home that night with one of the judges from the competition, someone I had known casually for years and was looking forward to getting to know better. We were hanging out at my place, on the eighth floor of an apartment building a block from the beach, when my buzzer rang.
It was Terry, my ex. She was very excited, and screamed at me through the intercom to get my ass downstairs as she had a surprise for me.
My new friend demurred quietly and exited stage left.
I went downstairs, where Terry was waiting outside the building. (Backstory: she used to live in the same building, two floors up from me, which is how we ended up together in the first place. After we broke up, she moved out of the building.)
She congratulated me, and then said, “Go and see who’s waiting in the cab.”
I go over to the cab, and Linda pops out of the window from the backseat, grabs me by the back of my neck, and shoves her tongue down my throat. As she is doing her best to pull me in the window of the cab, Terry grabs my legs and lifts them up, trying to shove me in through the window.
They both giggle something about kidnapping me away from my new friend. I then broke it to them that my friend had taken off when they had buzzed, so kidnapping wasn’t necessary.
Long story short, we ended up naked and in my bed a few minutes later.
So, trying to be chivalrous – for want of a better word – I fucked Terry first. But… and this is a very big BUT… while I was fucking Terry, I was passionately kissing Linda.
I was so fucking turned on, my first threesome, slamming away into my ex-girlfriend while kissing my incredible new lover, everybody screaming and moaning, and both Terry and I came pretty quickly.
There was some sucking and kissing, and very quickly I was on top of and deep inside Linda.
BUT I wasn’t exactly chivalrous when it came to my time with her. That is to say, I didn’t want to kiss Terry while I was fucking Linda. Linda was my turn-on. Linda was the main event. Linda was dinner and dessert.
We were so lost in each other that we barely noticed when Terry got out of bed, took her clothes, and must’ve gotten dressed in the living room. The first we knew about it, the door was slamming.
We came out of our bubble, looked around, realised that we were down one person, asked one another if we should go after her, but both agreed it was pretty futile at that moment, so we may as well just enjoy the time that we had together.
Linda‘s legs were wrapped around my back, my cock was deep inside of her, and that’s when the shit hit the fan. Technically, that’s when the purse hit the window.
There was a loud knock at the door.
Linda and I were loud enough that it’s possible that it was the most recent of several loud knocks, but either way, I slipped on my jeans, taking great care not to break my cock in half, and tiptoed to the door to look through the peephole.
It wasn’t Terry. It wasn’t my neighbours. It was my landlords. Technically, the building managers, a 30 something couple who had taken over about six months earlier.
I opened up the door affixing my most disarming smile to my face, and asked, “Is everything o—?”
But everything was not okay. One of them was holding up a purse that I immediately recognised. It was Terry‘s. Apparently, she had screamed like a deranged wounded animal when she got downstairs, and then pitched her purse through their floor-to-ceiling plate glass window on the ground floor.
So, yeah… Like I said in my first answer: I would definitely make sure that everybody got equal time, even if my passion for one of them was worn out whereas the other one was, to me, like mainlining Viagra and cocaine.

OH...MY....FUCKING...GODDDD!!! No exaggeration that this threesome debut was a complete disaster, of epic proportions How you made it out of there alive is seriously impressive though! I feel like you should be given some sort of Award for that at least... Crikey!

If it's ANY consolation, I think I probably would have locked Terry out altogether - or at least asked Linda too... Terry sounds like too much of a Stage 5 Clinger and way too loud and OTT for my liking! I can actually understand WHY you and the lovely Linda Lovelace blocked her out.

Are you 100% sure Terry wasn't a bloke...?!! She must have had a serious throwing arm and been lugging some VERY hefty purse/coin to have lobbed it through a plate glass window! I only ever managed to shatter the windscreen of my Highschool Phys Ed teacher's mini-van during discus practice. I admit that took some serious "talent" and miscalculation. But NO WAY could I shatter a plate glass window with MY purse. For two reasons, I'm not built like a Mother-Trucker. And...I don't have enough coin to my name Somehow I think Terry's vocals might have been the real culprit in this shattering moment.

My goodness...this has been THE most enlightening and hilarious read I have set eyes on. If it's ok with you I'm going to save it for future reference in case my threesome foray (which is still a figment of my hopeful imagination) goes pear shaped...or for whenever I'm having a really bad night and need to remind myself that some's had far worse. Poor Terry In all seriousness though, I really appreciate and love your complete honesty and epic story. I hope you are not still beating yourself up over this whole experience? And that Terry hasn't managed to track you down...?!

Thankyou for this story my friend

 

[soflabbwlvr]

My wife and I had been together a few years when we discussed fantasies. She was fascinated by my past, and I had freely discussed my dozens of sexual encounters with her. She had a bit of jealous streak, however, so I was a bit reluctant to discuss my desire for an FFM threesome. But she asked, so I told her. Her reaction was about what I expected - she shut down the conversation immediately.

Flash forward 10 years, and we're in bed on a Saturday morning after a round of morning sex. She was feeling particularly frisky, and told me she was ready to fulfill my fantasy. We fucked again and then the conversation shifted to who would be the lady? We settled on her high school/college best friend, a beautiful blond with a bubbly personality who exuded sexuality, and with whom she had a non-sexual encounter before we we met. The problem was that Marie lived several states away, and was busy living her own life. After a few months of trying to lure her to Florida for a visit and meeting no success, we gave up.

At that time my wife's job required her to work at a different location every day of the week. A gorgeous Colombian woman a few years younger than my wife started working at one of the facilities. Despite seeing each other only once a week, my wife and Dolores quickly became friends. My wife suggested Dolores as a candidate and after meeting her I quickly agreed. Unfortunately, Dolores had an insanely possessive boyfriend who did not allow her to have any life outside of their relationship. Two months after she entered our universe, Dolores abruptly quit her job and moved to NY with her boyfriend.

Once Dolores left we were out of friend-based options. We went to gay and lesbian bars, began scouring personal ads, and signed up on swinger websites looking for options. We contacted some women who were looking for the same thing as us, but after meeting and feeling no chemistry, we moved on.

After two years we finally found a woman who seemed promising. She was the right age (within 5 years of us), single, professional, and attractive. We arranged to meet at a restuarant to get to know each other over dinner and drinks. Due to prior experiences of meeting women with whom we had no chemistry, we went in with low expectations and agreed to meet for dinner, only.

Needless to say, the evening was great. We were as interested in her as she was in us. She mentioned that there was a hotel a few blocks from where we were having dinner. I called to reserve a room, and we were off.

Once in the room Christine suggested the women go to the bathroom to freshen up. The door closed and I heard the shower start. I undressed and wiaited on the bed. A short time later the women emerged freshly showered. My wife guided Christine to the bed. I kissed her while my wife went down on her. The rest of the night was spent fucking and sucking each other in every way imaginable.

When we woke up the next morning we resumed where we left off the night before. Eventually we cleaned up and left.

So, what would I change? At the time, nothing. It seemed perfect to me. But looking back, I'm sure my wife would have enjoyed someone with whom we had a prior relationship and genuine affection, rather than a near total stranger. I know this know, after 15 years of swinging with my wife. I love fucking strangers, but she prefers partners with whom there is a relationship other than sex.

 

[J_Bone]

My first was with two roommates that lived in my apartment complex in college. I was fucking them both, but separately. They both knew and there was no jealousy or anything since it was a totally casual FWB deal with both. In fact one had a serious BF and I was her late-night-booty-call-because-I-need-to-cum guy primarily because her BF couldn't get her there.

Anyway, they showed up at my apartment late one night together after being at a Roaring '20s themed party for their sorority. I was just hanging out watching football in nothing but a pair of gym shorts. They both looked great with all the '20s garb, short skirts with fringe, fishnet stockings, etc. They were a little tipsy and they sat on either side of me on the couch, both kind of flirting, asking how I liked their outfits and getting handsy. One started to kiss me as the other was rubbing her hands on my chest. Didn't take long to figure out what they were there for, a threesome. Jackpot!!

It was a little different than those I've had since because other than them doing a little kissing and some light petting with each other (don't believe either was truly bi), it was less about the three of us as it was about me just taking turns doing them both on the living room floor while the other mainly watched. We went a couple of rounds, then watched a movie together, then went again. Then one went home and the other stayed over. Definitely an experience and definitely organic from my standpoint, although they knew what they were planning.

Had quite a few others since and I'd say just talk to your husband about it, maybe hint at first. Gauge his response and get a feel with where he is. I'd think most all guys would totally be on board with a FFM/FMF situation. Although another guy in the mix could prove to be a bridge too far. Best of luck!!

 

[Shark9000]

My MFM was with two of my former co-workers. None of us were dating each other. It was meant as pure fun and it was just that.

There is nothing I would change. The times together were some of my favorite nights sexually in my life.

It ended when she met someone.

 

[Rockymtnman]

Haha! Sneaky little fuckers, planning to spring you like that Good on you for admitting "some" intimidation AND riding it out. Would have been fun!

Yeah, but they had me figured pretty good. They knew I was certainly “freaky” enough to not get wierded out by it being sprung on me. Honestly, probably better that way. Being distracted while using heavy machinery or working with 1500-2000 lb animals thinking about a 3 some might have been dangerous.

Performance must have been solid as I was asked back.

 

[MakeMeWetAF]

The whole saucy adventure sounds sooo Fuuckking hot!

Great!!! I'm now VERY hot and bothered as I I have an intense craving, an itch building in my pussy and I can't get to her now! Grrr
Fuck you very much for flicking that horny little switch deep inside of me...Grrr!!! Being patient really sucks when turned on!

I love horses and a good trail ride. I used to be a horseriding instructor in my spare time. I remember cutting through a huge farm paddock one day to get some sunset photos. I was so "in the zone" with my photography that I didn't see or hear a stack of horses venturing up to me - they were magnificent. I wasn't expecting this so was completely unprepared - no carrots or apples with me. It's like they couldn't care less that I didn't have food for them. They just surrounded me up close and stood there for a good 10 minutes gazing at me with their beautiful big brown eyes, two rested their heads on my shoulders. Man it was a beautiful moment!!! Soul stirring, gentle, trusting magnificence. So, sooo envious of you!

 

[AdriansDenOfIniquity]

OH...MY....FUCKING...GODDDD!!! No exaggeration that this threesome debut was a complete disaster, of epic proportions How you made it out of there alive is seriously impressive though! I feel like you should be given some sort of Award for that at least... Crikey!

If it's ANY consolation, I think I probably would have locked Terry out altogether - or at least asked Linda too... Terry sounds like too much of a Stage 5 Clinger and way too loud and OTT for my liking! I can actually understand WHY you and the lovely Linda Lovelace blocked her out.

Are you 100% sure Terry wasn't a bloke...?!! She must have had a serious throwing arm and been lugging some VERY hefty purse/coin to have lobbed it through a plate glass window! I only ever managed to shatter the windscreen of my Highschool Phys Ed teacher's mini-van during discus practice. I admit that took some serious "talent" and miscalculation. But NO WAY could I shatter a plate glass window with MY purse. For two reasons, I'm not built like a Mother-Trucker. And...I don't have enough coin to my name Somehow I think Terry's vocals might have been the real culprit in this shattering moment.

My goodness...this has been THE most enlightening and hilarious read I have set eyes on. If it's ok with you I'm going to save it for future reference in case my threesome foray (which is still a figment of my hopeful imagination) goes pear shaped...or for whenever I'm having a really bad night and need to remind myself that some's had far worse. Poor Terry In all seriousness though, I really appreciate and love your complete honesty and epic story. I hope you are not still beating yourself up over this whole experience? And that Terry hasn't managed to track you down...?!

Thankyou for this story my friend

Yeah, I don't know what was in that purse that night. Maybe she was a hammer-throw champ in high school. I mean, she had the shoulders for it, and we were only 19.
Please, go ahead and save it. I'm glad it was educational. Learning from our mistakes is the stuff of life, right, and learning from others before we can make those mistakes is pure gold.
There were two more threesomes that I learned from. I'll post those sometime over the weekend.
In the meantime, I am published on here now! Yay! Boat Cruise, in Loving Wives. It's not as good as the next one, but I'm having a publishing issue with the next piece for some reason, and the moderators have yet to give me any clarity as to the why. Ah well...
Have a good 'un.

 

[bobsch703]

My only time was a loooong time ago. I placed a personal ad in a newspaper - this was pre-internet lol. A couple answered, we chatted a little bit, met and a little later went to a motel room. He went to the bathroom, she undressed me and got naked, he came out and got in bed too. He started sucking me, I turned and got into a 69 position and sucked him too. He stopped and told her to fuck me, so she got on top and rode me for awhile. Then he told her to get off and he blew me until I came. The she got on top of him and rode him for awhile and then she finished him with her mouth. I started dating my wife a few weeks later and we never got together again.

 

[Boonerboy]

I need some expert advice. I've always fantasised about having a long and leisurely threesome. At first the fantasies were purely MFM however, my curiosity in women is increasing to the extent I'd consider an FMF threesome.

I suppose the thing that has stopped me from bringing my fantasy to reality is my concern that proposing this to my partner and anyone else I'd like to bring into a threesome may be met with shock or disgust or any other negative reaction.

While threesomes are a common fantasy for many of us, initiating them is a whole other ballgame (so to speak). I'm not sure what would be an acceptable way to dip my toe in these waters. In my mind's eye, I'd just love to have it play out naturally one afternoon (or even over a weekend away) if we had guests over, things got a bit frisky and one thing led to the other and we all just ended up having some naked fun exploring eachother and any shared fantasies. Maybe watching eachother as we all expose and masturbate ourselves, build up momentum, indulge in some mutual masturbation, and gradually fuck eachother and take turns watching, fucking and making ourselves come. Then have a lazy siesta and get at it again later in the evening. Any guidance on this or potentially hotwifey scenario would be wonderful. I'm so horny and wet I feel I could cum just writing this. Fuck it feels good. Please help this WET AF Damsel in Distress. She needs a good ravishing in the above way ASAP

Make sure you are comfortable with the third person you bring in. If you are worried about things being weird after, don’t pick a good friend. FMF is a lot of fun, though I’m a bit biased because I don’t find most men sexually attractive. But with the right partners both are fun, good luck on your journey!!!!

 

[cowboyup6977]

Mine was with my BFF at the time
She was always complaining about her husband messing around on her
A lot of pot and booze were involved
My husband is the only man to make me orgasm so I had the bright idea to watch them have sex so I can see how he does me stupid I know
I had never had any inclination for women and didn’t know my friend was bi
He was doing her doggie I was sitting in a chair playing with myself
She started crawling towards me
Got right in front of me and grabbed my hand and said please
I thought I’m in this far so I just went with it
She was very good and had me cuming in no time
I thought I had to return her favor so we switched positions with my husband know doing my doggy
Let me tell you the first time you get that close to another pussy you really don’t know if you can
I dove in like i knew what I was doing
I guess I did because she came twice
My only regret is she was hairy and I’m smooth and a stray hair ruins it for me

 

[NightL]

My ex-partner was traveling through our city and due to circumstance needed accommodation unexpectedly. I set up bedding and sleeping bag in the living room. Was a small house with our bedroom off that living area. We left the door open.

During sex with my partner I was hearing sounds from the living area. There is a distinct sound when someone is masturbating in a nylon sleeping bag .

I looked at my partner and in agreement I called out "come through".

I would not wish anything to be different from what evolved - it was magical.

 

[cjcurious]

Sorry Celand. I thought I replied to your response. Love your advice and observations. Thankyou so much

I spilled about some other fantasies I'd love to experience with Light of My Life while romping with him earlier. Should have seen the grin and twinkle in his eyes - can't wipe these from the bugger's face! His response to my indecent proposal was "Geeee whiz! SOMEONE'S got it ALL mapped out haven't they...??!" and to "Watch out because he can definitely see these things happening" Hopefully he'll have the same cheeky enthusiasm when I spring him on how he'd REALLY feel about a threesome...

I'm no expert, but my experience with sharing fantasies with partners has definitely spanned the full spectrum from one end to the other. And if your partner reacted like that to your sharing any fantasy, then I think you're in a really good (i.e. supportive) spot to share the whole truth about your feelings. Even if it is not the same full buy-in where he can definitely see those things happening, it sounds like it would be met with considerable care for your desires. So if it is not the reaction you hope for, it sounds like there is little chance of it irreparably changing things.

My advice would be to approach the subject from the frame of you caring about, and being turned on by, him getting pleasure out of the experience before anything else. In other words, you can only enjoy it if he's enjoying it too. Sometimes this dynamic is assumed, like 'well, duh, of course, because that's what love is.' But from my experience it needs to be explicitly communicated. Even if your partner knows it deep down, it still makes a world of difference to hear it from your lover's mouth.

Also this may be a more personal preference, but I've also found it helpful if the third person you're bringing into an established relationship really cares about the pleasure of both partners. That is, he/she is not there primarily to "get with" one or the other person in the relationship, but instead to experience both of you in the best way possible. Making this clear to your partner goes a long way is assuaging any fears they may have about the experience.

 

[lovedoublepenetration]

I was very young when I had my first gangbang. Am 40 now. It was my then bf's father and friends who initiated me to dps and gangbangs. I thank them a lot for making me hooked to dps.

 

[Shaglus_Ziegler]

In the nineties I lived and worked in Big Sur. Got off work one night and ran into a girl I knew who was with a sultry bigger girl. After a few minutes talking they asked me if I wanted to go to their house and get it on with them. I asked if they were serious and they said that indeed they were. I immediately told them I’d love to. They told me to get some condoms and then follow them to their place. I did and then we spent a couple of hours getting really wild. It was glorious. While fucking the woman I knew she whispered in my ear that she wanted me all to herself the next time. They called me over a few other times after that. And I did have separate solo sessions with each of them. Good times. Cheers.

 

[ShandyLeer]

Done 3 somes with 2 girls before, but first one with my MILF gf and another guy was a vacation experience out of the blue and completely spontaneous.

 

[Sgts19]

Way back before I was married 2 milf's picked me up and we went to their room. About 50 years ago but I remember lots of whipped cream and lots of orgasms. I was maybe 19? they were in their 30'[s or 40's

Present day we've had many 3somes &4somes...with the same people. I loved the MFM because I get off on how my wife reacted. 1st time we did it we were in a 69 and I was so close to getting her off with my tongue I wouldn't stop. My friend who was fucking her from behind came and gravity took over and I ended up with a mouthful of cum. But I stayed at it until I got her off.

FMF's I love lying on my back with one sitting on my face while the other road me.

 

[Elle4u2use2]

Watching tv and groping under a blanket while his roommate sat on other couch.
We went to bedroom to have sex.
I invited roommate in. I intended just for him to watch. His roommate joined instead and called me names. They both fucked me. While on my knees sucking his roommate, the main guy stood aside watching and jerking in disbelief

 

[Uncut1969]

Watching tv and groping under a blanket while his roommate sat on other couch.
We went to bedroom to have sex.
I invited roommate in. I intended just for him to watch. His roommate joined instead and called me names. They both fucked me. While on my knees sucking his roommate, the main guy stood aside watching and jerking in disbelief

Hot story! Black or white men my ebony vixen

 

[lifeis2short2b]

Not sure if you count this as a 3 way. But I will and it was perfect ( For me).
I met this woman at a bar, I had seen her there before, I got up the courage to chat with her. We hit it off instantly. We hung out laughed and got pretty drunk. I walked her to her apartment and she invited me in.
When I got inside her roommate was there watching tv. She recognized me from that same bar. After some small talk she said she was going to bed. Me and the woman I met went to her room and wow, I had my A game that night. She was let's say pretty loud. At one point I fell off the bed and the roommate knocked on her door and asked if everything was alright.
The next morning. Me being a freak and can't sleep past 6am got up and went to the kitchen to try and see if she had some coffee or tea. Her roommate came in and I said good morning would you like some tea, ( damn no coffee). She said no and sat down. I said your up early. She laughingly said who can sleep with all that noise. I apologized and she laughed again and said no her friend needed that. Apparently her friend was down after breaking up with her boyfriend months earlier.
We talked a little bit, and she made a comment a few times about how lucky her friend was. I'm pretty sure I was still drunk from the night before so I just went for it and kissed her. She was very receptive she put her finger to her lips as to be quiet took me by the hand and led me to her bedroom. She wasn't loud like her friend but it was probably for the better.
That's the closest I have ever gotten to a 3 way and as far as my personal opinion on 3 ways I think it was perfect. I had two woman technically the same night. I wouldn't change a thing.

 

[JBinFL]

Ours was easy. We went to have drinks, my wife started talking to this guy, and next thing I know we are in our hot tub as she’s blowing him. It got crazy and I wish I wasn’t drunk.

That was the first night I sat and watched her get fucked by a big cock. I remember that part lol

 

[ZOEOHZOE]

my roommate and her bf. kind of drunk when I found them fucking and joined in. most of what I remember is it was good and when he fucked me as I was going down oh her it was hot. yeah I would do it again

 

[JBinFL]

my roommate and her bf. kind of drunk when I found them fucking and joined in. most of what I remember is it was good and when he fucked me as I was going down oh her it was hot. yeah I would do it again

Ive only done MMF with my wife… well I’ve been with 2 women at a swing party, but I would prefer a more relaxed setting. But I’d do it again if I could lol

 

[georgerb]

Wife, sister-in-law and me...probably some booze involved and other forms of enhancement. Though the next day we were all leveled out and with knowledgeable purpose that repeated for a long time.

 

[Elle4u2use2]

Hot story! Black or white men my ebony vixen

Black