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My first (and to date) only threesome
Oh, the people you meet online!

Sounds almost like a book title by that writer, what’s his name…fine, I’ll stay away from sullying a children’s author’s name by linking it to my sexual experiences.

I’ll get to the point.

Life online is like a box of chocolates, you never know what…

Ok, I’ll stay away from paraphrasing movie quotes too.

I’ll cut to the chase – I met a woman online, and she wanted me to round out a threesome with her lover. Not her husband, but her lover. Complicated?

It’s sort of like math. It’s better if you break down the problem into its basic elements.

1) I was married and was looking to have an affair;

2) I went on a certain online site that caters to my kind of search;

3) I began an exchange of emails with a woman, who was also married, and looking for an affair;

4) I met this woman once, and she told me that she had been in a long term affair for several years already;

5) She told me that she wanted me for a threesome with her lover.

Got it? Ok, let’s move on.

After a few false starts, she disappeared from my radar. Things were risky, she was afraid her husband knew something, her lover’s wife had caught him, and so on. Short story – she and I met once, and that was all. Thirty minutes of talk. No sex. No affair. No validation of my parking ticket.

Fast forward several months. Out of the blue, an email comes to me from the woman. “How are you?” she asks, “I just wanted to catch up and see how you are…”

Out of the blue.

Some further email exchanges, and we agree to meet, just as potential friends, for coffee. Maybe dinner. I’m game. One can never have too many friends in this world. And she still intrigued me for some reason. Maybe I enjoyed being disposed of in such a summary fashion that first time, even without ever having become involved. Rejection can be a strong motivator for a man’s interest.

So out of the blue she is back. But no talk of affairs or sex, just friendship. Until I send her a sample of my writing – the kind of writing I post on this site – and all of a sudden she is getting hot and bothered. Makes a comment to me “too bad you weren’t interested in the threesome” – STOP RIGHT THERE!!

I write back and say “who says I wasn’t interested?”

Curiosity may have killed the cat, but in this case, curiosity fast-tracked matters, and within a week we were meeting again, a discreet half hour conversation ending with our first kiss. Hmmm…it was actually quite sweet. And it ended with plans to arrange the infamous threesome with her lover.

I’ve never been with a man before. That was not a concern of mine at all. I consider myself straight as the day is long – I love women and all the standard parts that come with their package – but I’m not a homophobe either. Sex is sex and love is love. I keep an open mind, even if I was not, using the common phrase, “bi-curious”.

The night arrives after much negotiation about place and time. They have been together for years, and they make the arrangements. I meet at the designated place and we walk two blocks to the rented room. Not the Ritz-Carlton, by any means. But not quite as bad as I would have imagined. No yellow police tape on any of the doors. Not yet.

We go into the room. Some wine is poured to relax the mood. It’s also poured to warm us up – the room is like an icebox. That is my only fear, that the cold will make my balls blue and my cock will shrivel up like a turtle retreating into its shell.

She finds the control for the radiator. The room begins to warm up. I can still feel my balls and cock intact.

Then there is that awkward pause. How do we start? I figure as the newcomer I have an obligation to show my true colors, so I begin, and I start to strip down to my briefs. Naked save for a small bit of cotton emblazoned with the word “Jockey”. We retreat to the bathroom, where both the woman and her lover pull down my briefs and turn on the warm water in the sink, taking some soap and giving my equipment a warm bath in their hands. They gently caress my cock, which is already standing at attention, and they fondle my balls which, despite the cold in the room, are hanging fairly low that night. They take a towel and dry me off, and we all end up out on the bed, with the woman’s lover getting naked first, and then she follows suit.

He takes me by my cock, in his hand, and moves his head close to my equipment, and then begins to lick and then suck on my cock. He takes me whole in his mouth and pleasures me, my first time being naked with another man except for sharing showers and change-rooms in gyms. His mouth feels different than a woman’s mouth and I don’t know if this is real or just my imagination, knowing that he is a man. But it feels good, firm and resolute, and he continues to suck me, but stops after a while before I can cum.

It is my turn to return the favor, and I wonder how it will feel, that first cock in my mouth. His cock is bigger than mine, a good inch longer, and definitely thicker, although his does not get as hard as mine. My cock is like steel – I know, there are lots of exaggerations in online stories, but what my cock may lack in size (and I understand from statistics, mine is average), it more than makes up for in firmness. His feels more like a somewhat stiff sausage, more pliancy and bend in it. I take him in my hands first, jacking him off slowly, and then I lean down and take him in my mouth. Hallelujah! I didn’t gag on it. But I can’t fit all of him in my mouth, and I wasn’t going to attempt to deep throat him on my first try.

Oddly enough, I feel nothing uncomfortable about the situation. It seems natural. Pussy and breasts are still my first choice, but there is nothing wrong with another man’s cock inside my mouth or in my hands. I suck him the way I would imagine myself being sucked, and I play with his balls too.

Then I feel it. Another mouth on my cock. She is going down on my hardness with a vengeance. She is a pro. I’ve never felt a blowjob like hers before, with incredible variations in speed, strength, direction – it is a virtual encyclopedia of fellatio techniques being demonstrated on me.

Her lover pulls out of my mouth so he can sit back and watch his lover minister to my cock. He is smiling, and his manner puts me at ease. I look down and see this beautiful woman pleasuring my cock with abandon, and it is a mystery to me how she got so good at what she was doing to me. I wasn’t complaining, though, and her mouth was exciting me in ways I couldn’t have imagined.

Then it stopped, and she lay back on the bed, spreading herself wide open to me and to her lover. He knelt in front of her and began to go down on her pussy, bare except for a small landing strip above. His ass was out in the open in his position, but I remembered that both had said they weren’t into anal play. So I just stood back and watched as he ate her wet pussy, watching as he spread her labia apart with his hands while his face was buried in her pink folds. Watching as he speared her pussy with his tongue and watching as she was writhing beneath him.

She came at least once from what I could see, and all the while, she had reached out to find my cock and she stroked it slowly to keep it hard. Watching her being eaten by her lover was all I needed to stay hard, and her hand stroking me was the proverbial icing on the cake.

Then it was my turn, and she knew from my email exchanges that cunnilingus was one of my favorite words. I took her lover’s place between her legs and began to taste one of the sweetest and wettest pussies I could remember. My face was pressed up hard against her, my tongue deep between the luscious pink flesh, sucking on her prominent clit and feeling her wetness bathing my cheeks and chin. I reached up and found her soft and full breasts and played with her nipples as I continued to eat her down below.

As I did this, her lover had taken my cock in his mouth again, and the sensation of this was incredible. I took my hands away from her breasts, and reached down to find his cock, still somewhat hard, and I gently fondled him and jacked him.

We took a short break. We talked. Her lover and I sat on either side of her as she lay on the bed, and we gently caressed her breasts and kissed her. She reached beside herself onto the table beside the bed and brought out a small foil-wrapped object.

We only had one condom. She had brought it along, just in case, even though they had made it clear that they were not sure, on this first meeting , how far things would go. Her lover offered it up to me, and as I put it onto my hard cock, I watched as he mounted her in missionary position and began to fuck her. I had never seen two people fucking before up close (other than watching myself and lovers in a mirror before, or watching porn – but that hardly counts). I was fascinated by the movements and fully expected this to continue until either one of them climaxed, but they stopped when he asked me if I had put the condom on, and I answered that I did.

I told her that I wanted to fuck her from behind, and she obliged, flipping over and offering me her ass in the air, and I could see her pussy just below her clean ass hole, still wet from her lover’s thrusts a moment before. I moved forward and brought my cock to the entrance to her pussy, and slid into her in a single thrust, trying to pick up the pace from her lover’s fucking. I increased my pace and reached forward under her to touch her full breasts which dangled and jiggled with every movement of our joined bodies.

No, I didn’t last for hours. No heroics. No tales of sexual prowess. I’ll admit it. I was so damn excited by all of this, and the feeling inside her pussy was so tight and incredibly wet, that I couldn’t hold it and I came inside of her, still wearing the condom, in about three or four minutes.

I stayed hard, though, and continued to fuck her like that for another two or three minutes, but I told her I had come.

This was the climax of the evening. I was the only man who had ejaculated thus far, and it was contained by a latex sheath.

I pulled off the condom, throwing it away, and returned to the bed to have her take my cock in her mouth again and taste me. This lasted for a few minutes and then we all took note of the clock on the wall. It was close to my departure time. I excused myself to the bathroom and took a quick shower to dispose of the evidence, in a manner of speaking. When I emerged, dried off and still naked, they were both lying on the bed beside each other, just relaxing.

I was still hard, and I took advantage of that by saying I had one more thing left to do. I have never been that much of an exhibitionist, and the notion of jacking off in front of two relative strangers was somewhat beyond my usual comfort level, but having been so intimate with these two lovers for the past hour or so, I let instinct take over from judgment.

I climbed up on the bed and stood over the two lovers, my legs astride their two bodies, and just above their chests, and I began to jack myself off. Not a slow and leisurely stroking, but a fast and furious blur of my right hand on my cock. I wanted to cum, and I wanted it to happen fast. My hand flew back and forth on my cock, as I looked down and saw the two lovers below me, watching me with smiles.

Odd things come to mind at odd times. This time it was Shakespeare. Julius Caesar, Act I, Scene II.

“ Why, man, he doth bestride the narrow world

Like a Colossus, and we petty men

Walk under his huge legs and peep about

To find ourselves dishonourable graves.”

I doubt my high school English teacher ever imagined that one of her students would actually recall the words of Shakespeare while jacking off in a threesome. I doubt I ever imagined that either.

And then my work was done. My cock spurted out its load onto her. It flew down and then dripped onto her breasts, around her nipples, onto her belly. My pearly translucent fluid formed pools on her body and traced rivulets as it dripped down her milky flesh.

I got down from above them and began to dress. In between briefs and shirts and pants and belts and shoes, I would come over and kiss her, and once or twice I would reach down and touch his now flaccid cock.

I dressed and said my goodbyes. They would remain behind, just the two of them, perhaps for more intimate goodbyes between them, perhaps just to clean up and discuss what had happened. But I said my goodbyes and left.

Walking down the street back to my car, the outside world would never have known what I had just done. I was just another anonymous stranger passing by other anonymous strangers, each with our own secrets that were never disclosed by the odd smiles on our faces.

I have no doubt that I had an odd smile as I walked those few blocks to the privacy and familiarity of my car. I still didn’t know the real name of the man with whom I had lost my same-sex innocence. I didn’t know if I would ever see either of them again. I didn’t know if I would ever do something like that again.

I didn’t know why I had even done it in the first place. I wasn’t ashamed of my choice. It had been very pleasurable. I just wasn’t sure why it had all happened.

It wasn’t as out of the ordinary as I had imagined a threesome to be. Maybe that was the biggest shock. Maybe I was expecting myself to be more shocked at my own choice.

I started the car and drove off. Still with an odd smile.

Oh, the people you meet online!

I think I was smiling because I imagined that those two lovers might be saying the same thing about me.

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