My 3rd Time


In my last story I told you all about my first time having sex with two men at the same time. That proved to be the spur I needed to move on from only lurking on a sexdating site to actually hooking up with other people than that one man I had been seeing regularly for almost a year now. And so, shortly before my 20th birthday, I had 2 more sexdates, during which I met three people that would remain my friends to this very day. Let’s start with the first one.

On a windy day, at the beginning of winter, I once again told my parents I was spending the night at a friend’s place. It was that friend I mentioned in my first story, the one who also did sexdating (and more!). By now I had fessed up to her that I had started doing these kinds of things, and she was okay with me using her as an excuse for my parents. Instead of cycling into town to her dorm though, I parked my bike near the station and took the bus to the next town over (that’s only about 15 minutes, the Netherlands isn’t that big.)

Wanting to be sure I was on time, I ended up being waaaay to early. After about twenty-five minutes my giddy excitement had been replaced by boredom and just plain being cold. That switch was immediately reversed though when a car parked across from the bench where I was sitting, and “N” opened the door and gave me a wave.

“N” was another older man (starting to notice a pattern?), nearing 50, but taller and more muscular than either “B” or “C”. But don’t let his appearance fool you, he’s a real gentle giant: soft-spoken and very cuddly. Of course, at the time I didn’t know that for sure yet, I just had an indication from his dating profile and the MSN chats we had had (or maybe this was after the demise of MSN and we used some other form of chat, I can’t remember.)

“Sorry I was five minutes late”, he said. “Were you waiting long?”

“No”, I lied, not wanting to appear silly.

In the car we quickly stroke up a conversation. About the journey, about school, about work… all very chaste. He quickly proved that he was soft-spoken, but he was also charming, quick with a joke and very interested in what I had to say. But I must admit I was a bit absentminded at the time, as I was wondering about what lay at the end of our journey: his house. And in there: his wife.

Yes, in this instalment of “My #th Time” I will tell you of my first time with a woman, which was also my first time with a couple.

I had seen pictures of his wife, let’s call her “E”. She was in her mid-40’s, with long brown hair and deep brown eyes. A bit small, looking miniscule next to “N”, but broad, with big breasts and a big butt. Being quite thin and having a nice a-cup myself, I was excited to be with a woman who had in many ways the opposite build from me. While talking with “N” I was imaging what his wife would look like when we arrived. Would she be fully clothed, like him? Completely nude? Wearing some kind of negligee?

Finally we arrived. As “N” was rummaging in his pocket for his keys, a neighbour of his passed by and greeted us. I gave a cheery yet polite “good evening!”. In my head I was secretly tremendously aroused by the realization that this man probably thought his neighbours had their cousin over or something like that, while we would be doing all these exciting things in secret! Realizing I was thinking about sex already, I tried to stop myself. Maybe things would be very awkward. Maybe there wouldn’t be that “click”. Maybe I would end up going home again without any sex. Don’t get ahead of things! Manage your expectations! But to be honest, it didn’t work. The idea of being with “N” and “E”, after years of merely looking at women in the swimming pool and wondering about sex with a couple, was just too enticing.

“E” had heard the keys turning, so just as I was taking my jacket of she came down the stairs. Not naked, nor in a negligee. She was wearing a denim skirt that I could almost, but not quite, look up while she was above me, and a low-cut green t-shirt that almost, but not quite, showed her bra when she was next to me. She gave me an enthusiastic welcome, with a hug and three kisses on the cheek, before gesturing me to move into the living room.

What followed was that bit of a sexdate that I’m sure you all really want to hear about: just talking to each other.

I joke, but it is of course very important to see if that chemistry from the chat translates to real life. So we talked. All three of us liked fantasy stories, so we talked about our favorite books, and whether the movie adaptations were any good. “N” and I shared a love for games. “E” and I shared a love for swimming. And so an hour passed. They had some beers, I had some cola with sweet liquor in it (they knew from the chat that I liked those and had bought some for me!), we ate some chips. Another hour passed.

Over those two hours my focus on sex slowly waned. That might sound bad for a sexdate, but it really wasn’t. We realized that we could talk about non-sex related stuff, which was crucial in us becoming friends, which in turn is probably why I still see them regularly years later. And while my focus waned it certainly did not go away. Whenever “E” would go to that kitchen to get something, I couldn’t help but look at her behind. And when she returned to the couch next to me, I could not help but sneak a peek at her cleavage.

Still, we didn’t talk about sex at all, so it was a bit of a surprise when after those two hours “E”, without any preamble, suddenly said “So… should “N” take you home, or do you want to stay?”

“What? Oh! Eh… No!”, I stammered. “I’ll stay! I mean. If you want me to stay?”

Suddenly her hand was on my cheek, and her face was right in front of me.

We kissed.

It was a great kiss, which lasted for ages. Whenever I pulled back, thinking we were finished, she moved forward, continuing our connection. Meanwhile, her hand wandered. From my cheek it slid backward, going through my hair. Then it went down, over my back and my side, to my leg. Then finally up again. I gave a shiver as I felt her squeeze my breast. It made me realize that I had sat there almost frozen up to that point, my own hands still folded awkwardly in my lap. Stiffly, as if moving them for the first time ever, I place them on her hips. Then I removed them again, and put them on the side of her head. She did the same to me, and our kissing became even more intense.

The kiss finally ended when I felt some tugging at the buttons of my pants. I looked down and saw “N”. While enjoying the view of his wife kissing me he had taken of his own pants without me noticing and was now doing the same to me. My panties (frilly and lacy, I do want to look good on a first date!) only got a quick compliment before they were removed as well. He place his tongue against my body, and I let out a quick sigh and a shiver, but before I could do more “E” was kissing me again.

We spend a long time like that. Me and “E” on the couch, kissing and fondling each other. “N” on the ground, eating me out. Somewhere during all that I touched another woman’s breasts for the first time. I loved it. I loved it even more when she then removed her shirt and bra (also frilly and lacy, also getting a quick compliment before it was flung to the floor). I continued to fondle, but she took my head between her hands and heaved her chest high, making it clear what she wanted. A bit awkward, being on the opposite side of this for once, I tried to mimic what “B” had done to me many times. I kissed her nipples, licked them, sucked on them… At one point I gave them a very soft nibble, as I personally don’t like anything harder than that, but she said I could do more. So I did what just about every man I’ve met tends to do, and went in way to hard! The third time proved a charm though, so soon I was enjoying he sighs of pleasure as I worked her nipples.

Eventually “E” suggested going upstairs. I nodded eagerly. “N” said we should go on ahead, and he would put away the drinks and chips first. I wanted to give him a quick thank you for giving head though, so I pressed myself against his body and we kissed for the first time. With him being so tall, his erection pressed against my tummy. Then I took “E”’s hand and let myself be led upstairs. Upon reaching their bedroom she pushed me onto the bed. It was an XL two-person bed bought especially with sexdating in mind. (Later, after I moved out of my parents’ place, I would start inviting “E” & “N” over to my place. To this day they complain about the width of my slightly-smaller-than-regular two-person bed 😛 ) She removed her skirt, climbed in after me and undid my shirt. Now both naked, we started alternating between kissing and playing with each other’s breasts. I still tend to leave the initiative to other people, so obviously it was “E” who eventually moved her hand further south and slid a digit into me. She slowly explored my body, and hadn’t gotten very far when “N” came in.

By now also naked, he climbed onto the bed on the other end, and suddenly his erection was right in front of me. We repositioned for easier access, and “E” and I started giving him head. Sometimes he was in my mouth, sometimes in hers, sometimes our lips where on either side of his penis. He proved very vocal in his enjoyment, moaning loudly, which I always like. We stayed in that position for a while, until he finally drew his wife upwards to kiss her. I also sat up and kissed him after they were done. Then I kissed her. Then this evolved in a weird three-way kiss. I remember marvelling at how easily we ended up in strange positions like this kiss or the double-blowjob. Over the years people who know I do this kind of stuff have often asked me about the logistics of threesomes. How do you know what to do? Honestly, it all happens very naturally.

For example, after our kiss “E” gently pushed me down on the bed again, then moved down herself, putting her head between my legs. “N”’s erection once again hovered over me, so it seemed to logical thing to do to take it first in my hand, and then in my mouth. Once again I was rewarded with some lovely moaning from him, but eventually he withdrew, gave me a quick kiss, then move to behind his wife. With nothing but a soft tug on her butt he indicated how he wanted her to move. When she was in the right position he slid inside and started to fuck her. I enjoyed this view and continued to enjoy the tongue and fingers at work between my legs, until “E” was so overcome with pleasure she couldn’t concentrate on me anymore. At that point I got up and stood next to “N” and I began to kiss him, meanwhile stroking his and “E”’s body with one hand each. All this went smoothly, without any planning ahead of time. It just sort of happens.

Because these things go so smoothly, with various positions flowing into one another, it gets hard to keep a chronology. So now we’ve reached the part of the story where I can’t tell which bit came when. All I can tell you is that we stayed at it for literally hours. Sometimes all three together, sometimes two (in any possible combination) while the third laid back and watched, perhaps only idly playing with themselves.

The only part that really sticks out in my memory began with me as the idle one. I sat propped up against some pillows at the top of the bed, while my hosts where fucking in the missionary position. I was simply enjoying the view when “N”’s penis accidentally flopped out. They used this moment to take a breather. “E” looked at me and said “Ah, look at the poor girl! She comes all the way over here and then we neglect her!”

Because I’m silly and often take things way too literally I started stammering out a response about how everything was okay and I was very much enjoying myself. I just kept on rambling like that until a smiling “N” kissed me to shut me up. It was another long, lingering kiss. “E” used that time to fetch a condom from a drawer. When “N” broke our kiss and leaned back, his wife placed the condom on him, unrolling it with her mouth. Then she removed my pillows, leaving me in a more lying down position, and just sat back, watching as “N” put his dick inside me for the first time. I didn’t know where to look, alternating between gazing deep into the eyes of the man lying on top of me and looking at the woman playing with herself while enjoying our show. Until she eventually felt like getting a little bit more involved, at which point she clambered on top of the bed, one knee on either side of my head so I could eat her out. I remember loving every minute of it, being ecstatic that this was finally happening and never wanting to leave.

So in the end I didn’t leave. After another bout of ever-changing positions “E” and I had both brought the other to orgasm with our fingers. I then laid back and relaxed while she and “N” had sex one more time, ending with him coming inside of her. After cleaning themselves up they laid down on either side of me and we started to cuddle. As we did I felt my eyes getting heavy. Eventually “E” asked “So… do you want N to take you home now?”

I turned to her, nuzzled against her, gave her neck a quick kiss and said, “If you want me to go.”

“You can stay the night if you want”, I heard her say right above me. In lieu of answering I merely nuzzled some more. She cupped me head in her hand and pulled my chin up so she was looking right at me, then gave me another passionate kiss, and that was that. Not long after someone pulled up the sheets, and I fell asleep nestled between the two of them.

The night was swelteringly hot, so I woke up several times. Every time I was excited to realize where I was, cuddling up to one of the people sharing the bed with me. It wasn’t my intention to wake them up, but it was of course bound to happen. The first time “N” groggily opened his eyes he only smiled, then turned around to continue to sleep. The second time he was much more awake and gave me another kiss. We both visible recoiled from the yucky morning breath taste of each other’s mouth, which caused us both to chuckle. He picked a bottle of water of the nightstand, took a swig, and offered it to me. Now almost fully awake we kissed again. As we did so his hand started to wander. Caressing my thigh. Squeezing my butt. Slipping between my legs, feeling me getting wet again… He reached over to the nightstand again, this time returning with another condom. “You want to go one more time?”, he asked. I nodded.

Obviously our rocking of the bed soon woke up his wife. She merely smiled when she realized what was going on. She caressed my face and played with my hair while I was gasping in the rhythm of her husband’s thrusts inside me but was too sleepy to do more. Secretly I was still quite sleepy as well. “N” finished quite quickly this time. While I hadn’t come yet, by the time he came back from disposing of the condom in the bathroom he found me back asleep, cuddled up with “E”.

I next woke up to me hosts getting up and getting dressed. One of them opened a window. I fell asleep again and could finally get some good sleep. The morning had ended by the time I opened my eyes again. I quickly threw on my bra and shirt, then realized I hadn’t seen the rest of my clothes since we had gone upstairs. I hurried down.

There I found “N” typing something on his laptop. “E”, it turned out, was off to a lunch-date with friends. I apologized profusely for oversleeping, but “N” just waved it away, saying they would’ve woken me if it had been a problem. He fixed me some breakfast (brunch really). He had already had his lunch but sat with me anyway. We talked about all sorts of light topics. Nothing sexual. He had pointed me to the rest of my clothes, but I had noticed how his eyes kept being draw downwards while I was talking to him, so I decided to be a bit naughty and had just sat down for breakfast leaving those clothes where they were. He tried to sneak a peak a few times but didn’t bring it up.

After cleaning up the table he sat back down on the couch next to his laptop. I crawled on top of him, whispering “I fell asleep before I finished this morning. Can I quickly fix that?”. He smiled as I quickly brought myself to climax just by grinding on top of him. Afterwards I gave him a peck on the cheek and a wink as I hopped off, grabbed my panties and ran towards the shower.

It was going to be a while before “E” got home, so I had to leave without saying goodbye to her. It didn’t really matter though, as in the car ride back home “N” and I already planned our next meet-up. During that ride we were completely chaste again, not showing anything to the outside world, but I was still relieved to see no trace that neighbour who had seen me go in.

When I got back to my bike I called my friend, the one I had told my parents I was staying the night at, to see if she was home. She was, so I went there and just raved about my experience of the previous night. It was one of the most exciting things I had ever done and just really needed to talk to someone about it!

Like I said before, I’ve stayed friends with “E” & “N” over the years. Some periods we saw each other often, for a few months even weekly. Other times relationships or full schedules got in the way. But we’ve always come back to each other. Just last week they were at my place, complaining about the size of my bed as usual but having no problem fucking me in it anyway. Over the years I’ve also experienced a few more firsts with them, so if this series continues you should expect to see them pop up every once in a while. It was with them that I first introduced a boyfriend I had met in “real life” to my sexdating hobby. It was with them and three other men that I had my largest group experience up to this point. But those are stories for some other time. And first I need to tell you about that second date I mentioned way at the beginning, which introduced me to someone who didn’t just stay a fuckbuddy, but who is actually one of my best friends to this day. See you all next time

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