Our First Threesome, Pt. 2
Chris lived in an apartment in a posh suburb. The place was painstakingly decorated with very luxurious trappings. As he put it, after a year in Iraq, he had no patience with living simply! He poured us wine, and we chatted uncomfortably while we waited for his roommate to leave.
Then, we were alone. We retired to his sofa, which was positioned adjacent to a large window. Looking out, it occurred to me that it was quite easy to see in. Mental note. Alison sat between us, and we each took another nervous sip of wine. It was clearly time to start something.
Chris, the expert, began us. He began us with a horrible, hacknyed line that made me laugh inside, but I don’t blame him–how exactly does one start a pre-arranged, sober threesome? Taking a sip of wine, he told us that “one of the best things about a nice merlot is how it tastes on someone else’s lips.” I smirked, but Alison gamely replied, “well, I guess I should see if you’re right!” He cupped her head in his hand, and leaned in for a kiss.
And we were off! I put my arm around her shoulders, and watched as they kissed each other, inches from my own face. Chris put his hand on Alison’s knee, and I did the same. She broke off kissing him, and swiveled around to kiss me. Chris watched us as intently as I had watched them, and out of the corner of my eye I watched his hand drifting up, her black dress creeping further up against her pale thighs. Alison leaned back a little bit into the couch and spread her legs apart more. Soon his hand disappeared under her her skirt, and she moaned into my lips.
Alison turned back to Chris and they kissed again, while I took my turn with her legs, stroking them and letting my fingers glide upwards, trailling my fingertips across her panties. I could practically feel her crotch throbbing. Meanwhile, Alison was getting busy rubbing her hands up and down Chris’s chest, and soon began working on his belt, and then the zipper to his trousers. Chris was working her tanktop off of her, and she responded by wiggling herself out of her skirt. We two guys were still completely dressed, but Alison, between us, was down to black bra, black panties, and black high heels.
It was at this point that I felt extremely out-of-body. Not in a bad sense. But I was having a little trouble being lost in the moment. All I could think was, my god, my girlfriend is about to reach in and take a hold of a strange man’s cock, right in front of me! Then I made the mistake of looking out the window at the street. Nobody was there, but I realized that everything we were doing in the brightly lit living was on display. Was that hot? I wasn’t sure yet. Maybe.
I felt movement next to me, and looked over to see Alison sliding down on to the floor, on her knees. Chris’s cock was out, and it was indeed very beautiful. More slender than mine, with a pronounced upturn at the end. As she slid down on to her knees, her hand was grasping his cock. Positioned, she flipped her long hair our of her face, looked intently at me, and went down. Chris groaned.
I slid over next to him on the couch, and Alison reached out with her hand to fumble with my pants. I unzipped and took my own cock out, and with her right hand, she began to stroke me up and down while sucking on him. Then she switched, licking me while rubbing him with her left hand. It was now that the out-of-body feeling subsided in favor of a very pleasureable, “my god, I am totally in a porn movie sensation.” Two guys sitting there with their cocks out, a beautiful women in her underwear working on them both, one by one.
Chris stood up, and I did too. Standing next to each other, our cocks were now almost touching. Alison, still on her knees, ran her tongue over both of us, pushing them together. She grasped the two as if their one, and tried for a moment to squeeze them both into her mouth. Unsuccessfully, but soooooo hot. Then, in a slightly suprising moment, Christ also got down on his knees, and suddenly took me into his mouth. I stared down at their two heads pressed together, as they playfully fought to get my cock into their mouthes. How did I get to be this lucky?
At this point our visibility in front of the window became acutely obvious, and Chris suggested we move upstairs. Alison went first, still only in her underwear, and Chris followed her, playfully swatting her lovely ass as she pranced up the stairs in her high heels. He lead us into his bedroom, which was mostly taken up by a large beautiful wooden bed, candles flickering on every surface.
Stayed tune for Part 3: Actual sex begins!
Our First Threesome, Pt. 1
First of all, apologies that these entries are running heavily tilted towards being written by me (George). The point of this blog is for us to be reminiscing together about past experiences, and hopefully to explore our two different (but highly compatible!) approaches to sex and sexuality in th econtext of a committed, lifelong, open relationship. But Alison is crazy busy right now, and I’ve got a lot of free time at the moment. What can you do.
Anyways, I think it would be nice to relate the story of our very first threesome. There is obviously so much background to our relationship that is crucial to these stories, and would in many ways heighten the eroticism. Hopefully over time, these details will fill themselves in. One thing you should know about the following story is that it was our very first time sleeping with an extra person. It was also Alison’s first time having penetrative sex with a man other than me. And finally, it was the first time I was with another man in a very long time!
We’d started with an ad on Craig’s List: I don’t remember the actual text, but it was something along the lines of “couple looking to explore, open to just about anything.” Our newly-inaugurated anonymous hotmail account was flooded with responses from men, some of whom we corresponded with a bit. One older gentleman offered to pay us $150 to sleep with him, which, to be honest, was tempting both for the money and the illicitness! But one email stuck out at us. It was from a guy about our age, who had just returned home from Iraq. To prove it, he’d sent us a picture of himself in uniform, holding a large gun. This is exactly what were looking for, frankly. Half the fun of meeting strangers for sex is the chance to meet people you’d never meet otherwise in your day to day life. We’re both latte-sipping members of the coastal elite, and neither of really knew any members of the military, let alone someone who had been in Iraq.
Plus, he was hot. His face was not his strong point, rough and cragged with protuding teeth. But in addition to the picture with the gun was another he’d taken himself with his arm stretched out. His body was smooth and clean-shaven, his muscles glistening in the flash. His cock lolled insolently out of a patch of red pubic hair. Clever move, that. Every time a guy sends you a picture of his penis, it’s always erect. Sometimes, when a cock is large, and perfect, and beautiful, that can work. But an erect penis shows every imperfection. You can see if it bends weirdly, or has a kink. Misshaven hairs are pushed into relief. Penises of the smaller variety show their inusfficiency. Any irregularity is pushed into utmost clarity by the rush of blood.
Not that you want a fully limp dick either. Nobody likes a limp dick. So our military friend sent us the perfect picture: stiffened, thick, but not fully erect. His cock was engorged with the promise of sex, but also implying there was more work to be done.
We wrote back, and then talked on the phone. Alison did the talking–I’m rather shy–and he seemed to be pleasantly surprised that she was in charge. We agreed to meet a hip wine bar nearby, promising that there would be no sex, just talking about what we would like to do.
I tell you, we were nervous. It seems silly now, but I managed to convince myself that our man was actually kids playing a joke. I was sure that we would show up at the bar and there would be some sort of Punk’d camera crew waiting to embarrass us.
Luckily, this was not the case. Our man–he’s clearly going to need a name, so let’s call him…Chris–turned out to be quite nice. Nervous himself, and with a goofy face. But he also had broad shoulders, and when he looked at Alison he would occasionally lick his lips unconsciously. He asked us what we wanted to do, and we hemmed and hawed. The focus, we explained, was to be on Alison. We wanted this initial experience to be about her, for the most part. Beyond that, we were open to just about anything. No anal for her, though, unless it was coming from me–we’d only recently started having anal sex, and her poor little asshole was nervous at the though of anybody else messing with it. And although both Chris and I were bi, this was a somewhat complicated issue for me at the time, and it wasn’t the right moment for me to be exploring that. Which was fine by him, I think–he’s in the military, and I could tell that his sexuality was…complicated. So, emphasis on pleasing Alison, whatever else happens is just bonus.
All bases covered, we set a date for the following week. We’d meet at his apartment. We’d bring a bottle of wine. And then, we’d all fuck.
Tune in later for Part 2!
A Stranger, a Car
We stopped the car.
We’d just met an hour before. I’d posted an ad on Craig’s list: my boyfriend is out of town, and I need to someone to give me a good, hard fuck. No strings attached, as they say. Dozens of men had responded, and I had a good time exchanging dirty emails and pictures with them. There was the teacher at an exclusive private high school. The businessman in town for the weekend. The lonely low-level administrator at a giant corporation. And then there was this man, who’d sent me pictures of himself lolling on a beach in Europe, and also fucking a bony little woman with a shaved pussy. I wondered who she was, but if he was up for some fun, so was I.
We had a beer or two, and made out some while leaning against my car. It was cold though, and like a wimp he asked if we could get in the car and go somewhere. Neither of us wanted to go to our apartments–I have roommates, god knows what he has at home–so I drove us to a dark parking lot. I crawled over into the passenger seat, fully clothed, and started to rub myself up and down on the erect cock hidden beneath his trousers. I was wearing a skirt, so it was just my panty-covered pussy gripping his crotch. It drove him crazy.
I took off my tank-top, leaving my bra on for the moment. Sliding down into the well of the passenger seat, I unbuckled his pants, and took out his cock. It was not bad, a little smaller than George’s, but nothing to sneeze at, and nicely proportioned. He was uncircumcised–come to think of it, I think he was my first uncut man! How about that.
His cock was hard, and I took it into my mouth, running my hands up and down the erect shaft. He reached around and unclipped my bra, and I let it fall free. My breasts are one of my favorite things about my body–I tend to be very body conscious, but everyone says my tits are to die for. So, why not work them some? I let his cock trail between them, as I moved up and down on it.
But, now time for the fucking I was advertising for. I took off my skirt and stepped out of my panties as best as I could, while he undressed as well, and put on a condom. No worries about the cold now! I clambered up unto of him in the passenger seat where he was still sitting. A little positioning, and I let myself sink down onto his cock. It feels good, but then I lean back against the dashboard and it feels even better. His hands are all over my tits, and I get that rush that comes from knowing a man finds you painfully hot.
Time to move to the backseat. As pleasant as being on top is, I tend to be on the submissive side when sex gets going, and I like nothing more than being fucked hard, especially from behind. Experience teaches me that a guy rarely takes the initiative to do so, so I get on my hands and knees, push my ass towards him, and tell him to fuck me from behind. He grabs me and pulls my ass onto his cock.
We go at it awhile, and he flips me over to fuck me just plain missionary. It’s nice and all, but you know, when a girl tells you to fuck her doggystyle, what kind of guy stops?! I want him deeper in me, so I put my legs up on his shoulder while he hammers away. Still not quite there, so I push my feet up on the ceiling of the card, trying to spread myself as wide as possible, tilting my pelvis up so that his cock thrusts even deeper. (Who says being submissive isn’t work!)
We fuck like this for awhile, and then I decide that it is time for him to cum, and that I want him to cum in my mouth. I tell him this, and he happily pulls out–to be honest, he was kind of running out of steam. I lean over his body, and start to cheerfully suck away, running my hand and mouth up and down his cock. He grabs my hair, which to be honest I kind of like, and finally gushes into my mouth.
It was hot. Never saw him again. He wasn’t a bad looking guy, or a bad fuck, but there’s a lot of guys out there in the world.
Looking for a Blowjob
I just had an incredibly successful Craig’s List experience. It was a Friday night, and I was horny. There is a long backstory here that I don’t want to get into right now, but what you need to know is that Alison is not here right now, and that I have been trying unsuccessfully to meet women or couples on Craig’s List for sex for a long time. I haven’t been in to meeting men recently (another story for another time), but this week, I got horny enough to give it a try.
So I posted an ad. “Straight man wants a blowjob,” it read, which is half true. I did want a blowjob.
I got a bunch of responses. Some had pictures, of which some were hot and some laughable. Some were conversational, some monosyllabic. One escort service wrote me. One guy sent me a picture of the glory hole he had constructed in his backyard pool shed. “Come over and watch some Str8 porn while getting your cock sucked!” he said.
But one guy seemed pretty normal and lowkey. Plus, hot. He promised me an “awesome blowjob” that would “start by licking your balls” and then a “wet bj to completion.” Okay, I could go for that.
With some extra encouragement from Alison, and my in-town friend Caroline, I wrote him back, and we set up a date. 8:00 on Friday, come “freshly showered.” The location was walking distance from my apartment. Easy enough. I gave Alison and Caroline all of the information, and told Caroline to call the police if I didn’t text her by 9:00 pm.
I showed up at the apartment, nervous out of my mind. I’m always like this with someone for the first time. I was with Allie when we first started dating, and I was with the various people Allie and I have met for group sex. What can you do.
The guy ended up being a shortish but very muscular Asian man, a bit older than promised, but not unattractive. He was nervous too, but he led me into his clean-as-a-whistle bedroom, and told me to take my shirt off. Be patient with me, I told him, this is my first time.
He had the lights turned down so low I could barely see his face, and he was playing Pat Methany quietly on the stereo. I laid back on the bed, and he took his own shirt off and began caressing me. First rubbing my shoulders, then slowly working his way across my chest, tweaking my nipples gently. I felt slightly ashamed of my body, as I always do with gay men. I’m in shape, but I’m not exactly buffed and toned. I don’t have the skill or patience to deal with my chest hair, and my WASPy self will never have a tan. But whatever, it was dark, and that’s why I’m not actually gay.
His hands, still roaming everywhere, he began to occasionally dip his fingers underneath the waistband of my jeans, brushing against my public hair and the tip of my cock. Not to be too narcissistic, but there are few things hotter than the place where low-slung jeans gives way to just a hint of dark curly hair and bare skin, even if it is my own waist! I stared in fascination as he trailed his fingers down my belly and under the waistband again, fully grasping my cock for the first time underneath my jeans. Finally he stood up and carefully took off my jeans and underwear, and stripped down to underwear himself. “Lay down,” he said, and I rather nervously did so.
He again began massaging me, this time nibbling my chest, circling my nipples with his tongue. He slowly worked his way down my chest, following the strip of dark hair down from my belly button, then nosing around my thighs as he crouched over my crotch. His hand began to brush my cock, which was beginning to stir a little bit.
He then pressed my thighs apart, and with a saliva-laden tongue began swirling around my balls, which I had just shaved earlier that day. I will say, the man knew what he was doing. Sometimes in these sorts of crazy situations I have trouble getting hard, so I just laid back, tried to relax, and enjoy the attention. Briefly, he came up for air to ask if I was enjoying myself. “Yes!” I replied meekly.
Back down he went again, and this time I could feel that breath of hot air that comes right before someone’s mouth engulfs your cock. Beautiful. Again, he knew what he was doing. He slurped his way all the down, and for the first time I involuntarily thrust up into his mouth, and he grunted. He wasn’t using his hands yet, just trying to swallow as much of me as he could. My cock is a little above average but nothing huge, but I’ve never been with anyone who could get the whole thing in their mouth. This guy had no problem, and soon I could feel his nose buried in my pubic hair.
Soon, he began using his hands, and after quickly glancing at the block, I realized we’d been at this for almost half an hour. Yikes! Time to cum. I started concentrating on orgasm, and he increased his pace as well. Soon, he started jerking me off in earnest, and soon after that, I felt that familiar rising sensation in my groin. “I’m going to cum!” I whispered hoarsely, as my breathing got increasingly labored.
He bobbed his head up and down even faster, and I felt myself let go. I didn’t even really feel myself cum in his mouth, which for me is always the sign of a good blowjob: just one seamless rush of good feeling, where you can concentrate solely on the pleasure and not worry about where you are cumming or what’s going on. He swallowed it all easily.
Afterwards, he had one final trick. He told me to relax, went to the bathroom, and came out with a hot towel that he draped over my limp cock. I have to say, neat trick! Ladies and gentlemen, you want to something nice for the man you just sucked off, a hot towel feels wonderful.
A brief hug goodbye, and I made it outside just in time to text Caroline that I was alive and not dismembered in a dumpster. Later that night, after having told Allie everything, I jerked off once more, to the memory of it.
