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As an experience I can recommend to all, I lived in a series of share houses for five or six years after the end of University until I moved interstate. Sure, there was the odd instance of insanity from housemates, yet for the most part I had a great run of friendship, fun, and debauchery. This was just as online dating was taking off as a common thing – it straddled that boundary of Tinder being viewed as solely a hookup app to one that most younger people seeking genuine dates would use regularly. Most of my housemates were single or casually dating other people and we’d all have boozy nights chatting about our love lives and egging each other on.
So I’m James, and to give you a little more background, I had started as a pretty shy guy when it came to women. I’d develop crushes on women from a distance though would rarely act on it, or when I did it would be in a cute but awkward way with women ‘out of my league’. No one wants to be ‘cute’ in that scenario, but at the least I now know that the idea of someone being out of your league is not always true. I’d had a few semi-serious and serious relationships by the point of turning 25, but it was only when I moved out of home into the share house that I properly grew in confidence. It all starts with a sense self-worth, right? Equally so for me, it was about having a group of male and female friends I lived with where we all supported each other and built up each other’s confidence.
In one of my more memorable experiences, I’d been casually seeing Sally for a few weeks – maybe getting onto two months. Neither of us were exclusive, although we were approaching that cusp of deciding if the connection would turn into something more. As pretty much all men do, I’d always desired a threesome – although I was a little uncommon in not being fussed if it were two men or women involved. So in the spirit of a footloose house, rather than having a serious discussion with Sally on whether we should start ‘properly dating’ I asked if she wanted to find a third for our bedroom.
Now I’d grown in confidence, but that still had it’s limits – so I asked her this in a text message conversation. We’d been teasing around fantasies, and she had asked about things we wanted to experience or try. I hadn’t put a lot of thought into asking this, and sort of blurted it out.
Me: *Well a big one for me is to have a threesome. I love the idea of experiencing something so different from sex between two – I think it would be really fun to explore.* (Nervous waiting intensifies) Sally: *Haha really? Like what, two women?* Me: *Ha – well sure, but I’d definitely be open to having another guy involved, though I wouldn’t interact with him myself. I guess it’s the dynamic between three people and how you connect that’s pretty fascinating, if that makes sense?* Sally: *Mmm that does sound delicious.* (more nervous waiting with the ‘Sally is typing’ at the bottom of the conversation, seemingly for hours) Sally: *I’ve never been with a woman but that’s something I find pretty intriguing.*
And we’re off to the races. I was on board, Sally was on board – but neither of us really knew how to find the third, aside from becoming that weird couple on Tinder where people you know might see you. Enter the housemates. At this stage I volunteered at a charity, and did a bit of work here and there, and spent the rest of the time in leisure – that day was lazing in the backyard with my housemate Jenny. I’d laughed and grinned when Sally had said she was keen and when I explained why to Jenny, so did she. ‘You’re kidding? You dirty man James,’ she said while I protested my indignation. We had a decent amount of banter, mostly on how were we going to possibly find someone. Then things got even better.
‘I know someone who’d be keen,’ Jenny said. Turns out Kylie, one of her high school friends was incredibly open, sex positive, all the good things when you’re looking to explore as a mid-twenties guy. And the best part was I’d met Kylie, and we got on like a house on fire. The next few hours were this back and forth of texting between four people with Jenny acting as the middle-woman to connect us, a few photos (safe for work, sorry all) going back and forth, and an agreement that the three of us should meet at a house party the following weekend.
It was one of the longest few days I’ve had to wait.
The house party was great – a little more civilised than most I’d been to, as the hosts even got a band they were friends with to put on a short concert. Picture those Bon Iver Take Away shows but with a far less famous folk trio. Better yet, the three of us got on amazingly.
I didn’t need to imagine what Sally looked like nude – I knew. She was tall, nearly at my 185cm’s (a little over 6 foot), and quite slender. Her pale blonde hair nearly touched the bottom of her shoulder blades, and when she was riding me in bed it was a sheer curtain over her small breasts and perky nipples. Of course at the party that was all covered up. She was wearing istanbul travesti a summer dress, floral patterned and elegant that came to just above her knees. My mind was filled with the thought that she had chosen that to impress Kylie. If my reaction was any guide, it would.
Kylie was an unknown. I knew already, and my eyes that night could tell she was beautiful – the dress she wore was tighter than Sally’s, and showed off her curves. It was more than that with Kylie. She was one of those magnetic people with an understated charisma that held your attention. And you wanted hers. Both Sally and I found ourselves matching her quiet voice, leading the three of us to move from the initial nervous stance spread across a corridor, to a more intimate circle, less than an arms length between us.
Over the night the three of us ebbed and flowed away from each other. After a fairly short time I knew the spark was there, yet the uncertainty on what would happen next remained. Sally and I found ourselves around the small fire in the backyard (it was summer, sure, but what’s an Australian house party without a fire pit?), my arm around her. We didn’t need to say anything – I could tell by looking at her she was on edge, and incredibly aroused. She met my eyes, smiled and nodded.
We joined Kylie in the kitchen, her holding a plastic cup of red wine and chatting to a few friends. I’m not entirely sure who said what, or to whom, but we found ourselves in a taxi-van back to my place, with my housemates, Sally, and Kylie.
All of us ended up in our kitchen, new drinks, and chatting with music in the background. It was a rather odd feeling with anticipation between the three of us building and most my housemates also knowing we were about to go into my bedroom and fuck.
We were sitting in my room, the two of them on the edge of my bed and I on my desk chair. I’d put music on – Massive Attack, or something similarly cliched. Kylie asked us what we were looking for, why we wanted to find a third, and why her. All of us were more than a little tipsy, and the conversation doesn’t stick in my mind, yet I do remember we felt the same. Sex is great fun, and best when it comes with a connection and respect, and we don’t need to be possessive about pleasure. I do know the tension was getting unbearable.
Sally told Kylie she hadn’t ever been with a woman. Each of us had our hands gently stroking other’s legs. Sally and Kylie kissed. It was soft, a little tentative, and bathed in the soft light of the lamp one of the most beautiful things I’d seen. Their hands entwined, and Kylie put her arm around Sally’s waist. I watched, not wanting to break the moment – this was Sally’s first kiss with a woman and she should have that to herself.
It seemed an eternity later that they turned to me, and the three of us traded kisses. My mouth slid from one to the other, along Kylie’s neck as they kissed and behind Sally’s ear, my lips met Kylie’s, Sally moved from my jaw to hers, then up to join us as the three kissed at once. It was a wonderful mix of awkward and electric, that feeling of being with and kissing a new partner for the first time multiplied a hundredfold.
Kylie stood up and took us with her. She was experienced in sharing, and her taking the lead flowed beautifully. Hands running over each other, stealing kisses as we went, we stripped to our underwear. You always imagine it would be graceful and erotic, but of course it was flavoured by eager nerves and a growing sense of urgency.
Kylie was stunning in a casually lacy bra and underpants. Unlike Sally’s slender frame, Kylie had wonderful curves and her breasts were a large handful. Kylie kept saying how lovely Sally was, leading to blushes and smiles, and when Sally said the same to her, Kylie grinned and kissed her. I unhooked their bras as they kissed, their arms dropped and the thin material fell to the floor. Their breasts touched as they came together and circled their bodies with searching hands.
I was hard as I’d ever been. Since this time I’ve had other threesomes, and with these two women as well. Yet there was something especially arousing about being there for Sally’s first time with a woman. I get it – typical guy, drooling over lesbians – though it lent an extra frisson to the night, something both Sally and Kylie agreed when we spoke about it later. I also genuinely cared for Sally, and took pleasure from her own joy. Sally told me that knowing everything that would happen that evening was a first for both her and I added a continuous and building sense of anticipation and eroticism.
They laid down on the bed, tangled together, alternating kissing and staring at each other while their hands trailed over their bodies. I knelt down on the side of the bed – I wanted to be a part of this too. Pulling their underpants to the end of their feet and dropping them behind me, I leaned between Sally’s legs and blew gently on her. She started, giggled, and they both looked down istanbul travestileri at me as I slid my tongue along her pussy.
We kept on, I moved from Sally to Kylie, kissing and licking as I teased the other with my fingers. They were moaning, mouth to mouth. I remember Sally laughing as a new feeling overtook her, and then going very quiet as Kylie reached down and touched her for the first time. I sat back on my heels and watched as Kylie’s moved her head to Sally’s chest, her lips sealing over her erect nipple, and ran my hands up and over Kylie’s smooth butt.
We switched places, Kylie and I. As I wrapped Sally in my arms her breathing became heavy and then hitched – right at the moment a woman’s mouth first settled between her legs. It sounds a bit Mills and Boon, but I guess cliches are that for a reason – I remember her clutching at me while Kylie went down on her. Her back arched, and her hands roamed over me, one into Kylie’s hair, down on to grab at the bed sheets – she seemed unable to control where they went.
In porn, I suppose it would be here that Sally had an earthshaking orgasm. I wish that were true, though it did happen later. She told me after she felt that she needed it to break, but the nerves and anticipation of the night had her too wound up to tip over the edge.
We shuffled around, and the next half an hour was a blur of limbs and hands and mouths. I know we moved into a circle on our sides, each of us going down on the other, Kylie to Sally to me on Kylie. That stood out as one of those unique feelings that only happen with more than two people in a bed – reciprocal pleasure not just one to another but shared among more. Kylie came – it turns out she’s one of those lucky people who come easily. Somehow, I held out.
At some point when Sally was on her back with my cock in her mouth, Kylie moved up from between her legs to lay along side and kiss her neck. ‘I want to see you two have sex,’ she said as she looked up at me, whispering into Sally’s ear.
Another blur of limbs and Kylie was on her back, Sally resting on her knees over her and looking back at me as I ran my hands down her back to cup her pussy, a finger sliding inside. It was one of the less graceful moments of my life when I stumbled into a spot between their legs and rested my cock against her. She gasped as I entered her, then turned to look down at Kylie. An odd, but unforgettable comment came next: ‘Mmm, get up into my grill,’ said Kylie, linking her hands behind Sally’s head and pulling her down to kiss. As I fucked Sally, their hands roamed each other and I felt Kylie’s fingers slipping over my cock in search of Sally’s clit.
I don’t know how long it lasted. I know Kylie came again. I know they kissed and moaned, their breasts either pressed together, held in our hands, or by our mouths. The feeling of their bodies below mine, of Sally’s back arching as she finally had her release, the build of tension as my own orgasm came closer – it was like nothing else. Sally later said it was the most intense thing she’d experienced in bed – me inside her and kissing her back as she kissed Kylie and felt her fingers below. I can’t say I disagree.
It didn’t last. Sally knew I was close. One of the things I loved about sex with Sally was her enjoyment in finishing me with her mouth. And this time she had help. I’d always dreamed of a double blow job – unfortunately I didn’t really get to fully experience it this time. With the two of their stunning faces meeting over my cock, and after a few brief licks and kisses, I came, Sally taking it all and swallowing it down, as Kylie kissed her neck and they both stared at me.
I didn’t get the full double blow job experience, or have sex with Kylie – that night at least – although I wasn’t going to complain. It was nearly 3am by this stage, and after a long session of playing, enough alcohol, we all crashed. It was more than enough for all of us in that moment, and overwhelming in its intensity.
We slept in the bed together, Sally in the middle with Kylie’s arm thrown over her body, and the sheets rumpled around us. I woke up to that, with a sore head and a grin on my face. I drank in the view and did the best I could to sear it into my mind. After a few minutes, I ran my hand over Sally’s and saw her eyes open and squeeze shut again.
‘It’s too early.’
‘It’s past 10 Sally.’
‘Mmm too early,’ she said, and turned to nuzzle into Kylie who barely stirred. I tucked the sheet over them and got up.
Most of the housemates were out of the house, Jenny included. I think I was glad for that, as loose as our household could be, there is something a bit odd about chatting to your housemate when her best friend was nude in my bed in the arms of another woman. Matt was lounging on the couch in the kitchen and looked up with a grin on his face.
‘Lucky cunt.’ I returned the grin with a finger, and went for a shower.
By the time I returned to my room the two girls had travesti istanbul stirred. They looked up at me, Kylie standing by the bed and gradually getting dressed.
‘We’re going out for breakfast. Well. Brunch I guess.’ I must have looked a bit crestfallen – I assumed she meant the two of them. Remember what I said about building confidence? Yeah, doesn’t come at once.
Sally smiled at me. ‘You’re coming too James.’ They both laughed at the uplift in my spirits and continued getting ready. I lent over and gave Sally a passionate kiss and when I sat back up Kylie was there too. ‘Got one more in you?’ and leaned in to meet me.
We walked down the street chatting, but I don’t really know what we talked about. All I remember is my mind racing with excitement – we’d clicked, we’d all had sex (well mostly), and yet we were still hanging out. And that kiss?! What if we get to do that again? That train of thought continued most of the morning, although by the time I had some food and coffee in me I was able to pay more attention to the two of them.
Which only got me more intrigued. The three of us were really clicking. Last night we had chemistry and that remained, yet the conversation had sort of blurred – we were a bit overwhelmed with the potential for what might come. Today we were connecting at more than a sexual level and I had to rein in my visions of a permanent group arrangement.
Of course that’s not really something you can do – you tell yourself that you’re not going to leap to assuming a certainty in personal relationships, or fill yourself with hope that the fashion model beauty you saw on the train wants to marry you, but your mind still fills in the blanks. And hope springs eternal, after all.
At one point Kylie blushed and looked down. Glancing around (we were in the corner, but it’s a busy Saturday morning), she leaned forward and whispered to us. ‘You know, I keep thinking about last night. You two were so good together. And… I guess…’
Sally looked over at me. ‘I mean, it was great. But not really all that fair. You didn’t get James yourself, did you?’ She reached over and took Kylie’s hand. I don’t know where her nervousness about being with a woman had gone.
Kylie met our eyes and smiled. ‘Your place or mine?’
Great in theory. But Sally had lunch with her parents, and Kylie remembered that she needed to get a present for her nephew’s birthday party the next day. And I had a date with another woman that night (I know, I know – why did I keep that date?). We couldn’t meet up til Tuesday.
Jenny, Matt, Ben and Jill were all home Saturday night (pretty ordinary date so left after a drink) and we had a good gossip. We never really shared details of what went on – it was always more about who, how we met, what we thought about them. The conversations like ‘Nah, he’d be an idiot to knock you back Jenny. Just ask him.’ So they asked how it went, and left it at that. Until they wanted to know how Sally felt about it all, and if the two of us would still hook up.
‘Well, yeah, I think so. We’ve got plans Tuesday night.’ There was a bit of celebratory laughter, and I added ‘To have a drink with Kylie.’ The laughs turned into hoots and looks of disbelief. I love those people.
Sally came around on Sunday afternoon for a quick fuck where she largely just talked about how good it felt to have Kylie in bed with us.
‘It was so intense. When you were inside me, and I was kissing her, her hands on my breasts? I just… huh… uh… haven’t felt something like that before, you know?’ I somehow held off coming while she relived that moment.
Tuesday rolled around, one of my volunteer days. I know time can drag, but this might have been worse than the first time. Now I knew what was coming and the nerves were building.
We met out, a suburb in between all three houses, and got cheap Vietnamese food with a bottle of wine. It felt odd at first, like there was a barrier between us. At one point we had a silence of nearly a minute and not that companionable pause in conversation because you’re eating.
‘You know, I think we might be a bit awkward because this is so unusual. This is kind of like a second date, but with three people, and how many times does that sort of thing happen to you?’ I could be a bit blunt at times, but it usually went down ok. ‘Sally and I really clicked with you Kylie. And you’re incredibly sexy. But there’s no obligations – let’s just enjoy dinner, yeah?’ And I leaned over to kiss Kylie behind the ear and whispered ‘Although I hope we continue on.’
She blushed bright red. I don’t think I mentioned earlier – Kylie has wonderfully milky skin, silken smooth and pale – so the blush went right down to her prominent cleavage. She’d dressed to impress.
‘Yeah,’ she said quietly, but smiled at both of us. A pause held for a bit, and the conversation began to flow again.
After we’d finished and wandered outside, we walked up the street a little ways in that aimless wandering that happens when no one is sure how to take the next step. We got to a quieter part of the street, I was a few steps ahead, and I turned back to them, swinging a foot about with a vague idea of proposing another drink in my mind.
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