My 2nd Time

This isn't really the story of my 2nd time. I couldn't tell you every detail of every sexual encounter I have had. Instead, this is the story of the next big step in my sexual adventures after my 1st time. I'm just calling it "My 2nd Time" because I like the naming convention :P

Last time I told you all how I had finally had sex for the first time. After it was over, while we just laid on the bed for a while, “B” suggested that I could come over more often. Spring was just beginning, and his house had a big garden that nobody could see into, so I could come and do some naked sunbathing. Now you should know that I was (and still am) a huge nerd, who enjoys boardgames and reading fantasy novels. I’m a very indoorsy person and I’ve got very stereotypically nerdy pale skin, so I’ve never considered sunbathing for fun. But I knew that coming over for that would lead to other things, so I readily agreed.

In the end it wasn’t even that great a year for regular sunbathing, so quite a few of these dates turned out to just involve indoor fun anyway. But sometimes the weather was kind, so I do have fond memories of times just lying naked on a beach chair with a book and a drink, with “B” in the chair next to me, also with a book open but with his eyes focussed on me the entire time, his dick sticking proudly into the air. In the end there was always a moment where he would suggest going to the bedroom. Or he would just move my legs aside to start playing with me. Or I would just suddenly find that erection of his hovering quite close to my face. As someone who had never gotten a whole lot of attention from the boys (or the girls), this feeling of being irresistible to someone was amazing, and I must admit I would milk those stares for all they were worth, always waiting for him to come to me, even if I was already getting aroused myself.

When it was too cold to sit outside our dates would usually follow what I call the “standard sexdate script”: pleasant conversation about everyday subjects over drinks, a short awkward silence eventually broken by a “Well… shall we?”, then wonderful sexiness. Those sexytimes also saw another couple of firsts for me. My first orgasm from intercourse (yay!) My first actually-on-my-face-facial (yay!) My first time anal (Meh...) My first time getting my ass licked (Sorry, I really don’t get the appeal. And I made him wash his mouth before kissing me again!) My first time wearing fishnets (I felt like a proper pornstar, and given what I just told you about how I like being wanted, you can imagine how much I enjoyed the look on “B”’s face as I wore them!)

For almost my entire 19th year I did not do any other sexdating. Why wade through all those boring or outright unpleasant messages when I already had someone I could have fun with? I stayed on the site though, and kept on the lookout for women and couples, since that was something I still really wanted to experience, but it would take almost all year until I found a couple I was comfortable enough with to meet up. Before that though, I met my second sex partner through “B”…

Half a year had passed since that first time we really had sex, and summer had come and gone. “B” had continued meeting other people, mostly men (those are always available in abundance on sexdating sites.) I guess he had been bragging about having a much younger girl as a fuckbuddy, as he eventually told me that several of his friends had voiced their interest in dating with the two of us. The idea of being with two men was exciting. The idea of watching two men together perhaps even more so. “B”, not being a dummy, of course suggested the idea during foreplay, when I was longing for sex the most. Obviously, I said yes. But I wanted to get to know the person first.

“B” had a couple of suggestions. Some I rejected just on looks. Which you might find shallow, I guess, but if there is no physical attraction sexdating is just not going to work. Some others I chatted with a little online, but with most of them the conversation would just quickly ground to a halt. Either they only wanted to talk about sex, or they didn’t know what to say at all. Eventually there was 1 person left, who I did get along with over the chat. Let’s call him “C”. “C” was in his late 30’s, so about 10 years younger than “B”, but still far older than I was. We chatted for a while, and eventually I told “B” that it would be cool if he invited his friend over for our next outing.

I went over to “B” on a gloomy autumn day. He picked me up from the bus stop. Normally our meetings started out… what would be the word? Platonic? Chaste? Anyway, we’d just say hi and talk about the weather and the like. No hanky-panky until we were behind closed doors. But this time I was far too excited to talk about the weather or the traffic. All I could manage was a curious “…and?”. Despite my brevity “B” knew exactly what I meant. “He’s waiting for you at my place, and is very excited to meet you”, he said with a smile and a giggle.

The next few minutes passed in silence as I just shivered with anticipation, until “B” managed to force the conversation open with some questions about university. Thus I was in the middle of a story about an upcoming test or something boring like that when I entered his house… and fell silent as “C” rose to meet me. He shook my hands, gave me three kisses on the cheek, and introduced himself. He followed that up with “Nice to finally meet you. “B” has told me a lot about you!”

“Oh did he? Only good things I hope?”

“Only good things. But they are perhaps better mentioned later on the evening.”

He scored some points with that. Someone showing blatant, undisguised lust for you can be really hot, but to me that only works if I already know someone. Otherwise it quickly comes across creepy or desperate. So his response, showing playfulness but also restraint, struck the right chord with me. That said, this time I was very excited to try out something new, and I had a person I already knew present in “B”, so I may have moved a little quicker than I usually would when meeting a new person.

Our conversation started with the usual spiel about our day, school, work, et cetera. But before long I was asking questions about “B” & “C”’s previous meetings. How long ago did they first meet? Did they see each other regularly? Nothing really explicit, though sometimes a more exciting answer was given. Like when I asked whether they always met up here, and the answer was “Usually. But sometimes at my place. And sometimes somewhere outside…” Obviously that prompted a follow up question from me, and before long I was listening baited breath to the stories of his adventures in sexdating.

This went on for a good hour and a half. Sometimes the conversation would suddenly veer back to a perfectly innocent topic, like the news or sports, only to end up back at the difference between kissing men and kissing women. I had made a good selection, as he turned out to be a charming man, very chatty, and obviously very sexual but never pushy. Honestly, we could’ve talked all night. But in the end “B” was the one who couldn’t hold back anymore.

When a short silence fell after a conversation about the first time he and an ex had dated with another man, he chimed in with “Maybe she would like to see that in action?”. A bit obvious perhaps, but nice and to the point. I giggled and said “I’m watching…”.

“B” got on his knees and passed his hand over the middle of “C”’s pants, where I had already noticed some swelling over the course of the story. He opened the buttons and took out the largest penis I had ever seen (This is a thing people write in sex stories right? Ignore the fact that it was the second penis I had ever seen ;)) Then he got to work.

“C” just reclined in his chair and enjoyed himself. Sitting on the couch opposite him I did the same. Except I kept my eyes open, as the hottest thing I had ever seen was happening right in front of me. Without breaking line of sight, I undid my flies and slipped my hand into my panties. Things played out as “B” and I had agreed before the meeting, with the men getting into the action first to ease me into things.

After a short while they switched positions, also shifting to another chair to give me a better view. Now instead of the back of a head I could actually see the cock disappearing between another man’s lips. “B” didn’t close his eyes though, he kept them fixed on me. I smiled and took of my pants and panties altogether, to give him a bit more of a show.

This was another scenario I could’ve stayed in for the rest of the night. I guess I’m a bit of a voyeur in that way.

I don’t know how long we stayed in that position, but it felt like a blissful eternity. Eventually B helped C up, and kissed him. Despite having just seen then suck each other off, the sight of two men kissing still made my heart flutter. C then spoke some hushed words to his friends, which I couldn’t quite make out, but C turned to me as B walked off and got something to drink. “Shall we go upstairs?”, asked the man I had met about two hours earlier. I nodded eagerly.

I went up the stairs first. In the bedroom I turned around and we stared in each other’s eyes for a moment as we embraced. Then we shared a passionate kiss. I took of my shirt and bra and laid on the bed wearing nothing except my ankle socks. He climbed on top of me with nothing but a shirt on he had unbuttoned on the way up. His pants had been left behind somewhere downstairs. Again we kissed, and I could feel his erection pushing against my leg. When our lips parted I said with a wink that he should get me a bit wetter first. His face disappeared from sight. I arced my back and let out a deep sigh as I felt his tongue between my legs.

At one point I closed my eyes in pleasure. When I opened them again I saw B had entered the room. He sat down in a comfy chair with a great view of the bed. He winked at me and started to stroke his penis. We were building things up slowly. Luckily he also liked to watch.

A short while later (you’re going to hear me say that a lot more, as I completely lost track of time at this point) I saw him rummage through the nightstand drawer with his free hand. He took something out and tossed it to me. The condom landed squarely on my chest. The hint was clear. I gingerly took C’s head in my hands and indicated him to come back up. We shared another kiss, and then I showed him the condom. He took it from me with a huge smile on his face, and gave B a quick wink… a few moments later I felt the second erect penis I had ever seen enter my body, as the first stood up enthusiastically only a few feet away.

After all that build up it felt amazing to finally just fuck. First he bent over and we shared a long, long kiss, as he kept fucking me and I wrapped my legs around him. When the kiss finally broke, he moved into a more upward position and put my legs to each side, and later in upwards, with my feet next to his head. My head rolled back from pleasure. I looked back up when I felt more pressure on the bed, and suddenly there was another penis there, hovering next to my face. B was finally ready to join us. I took his erection in my hands and gave it a quick kiss, but before I did more I spend a moment staring up, where the two men, who at that point formed my entire universe, shared another passionate kiss. Only when that broke did I move B’s penis from my hands to my mouth. I was immediately rewarded with a grunt of pleasure.

I’m afraid that at this point my sense of chronology deserts me. I think C eventually bend over again and started sucking B’s cock with me. At times it would be in his mouth, at other times in mine, and in between we would each have our lips on one side. It could also be that this happened later though, as after B had climbed in the bed we went through several positions several times.

For a while the three of us were just lying in bed, cuddling and kissing. There was another period where I just laid back to watch them suck each other off, first alternating, and then getting into a 69 position. There are two parts I do remember very vividly though: the first time seeing two men fuck, and the first time being fucked by two men. I just don’t remember the order…

Let’s start with that first one. During a moment of “downtime”, C was lying on top of me, but we were just kissing and cuddling. B had gone of to… I dunno. Get something to drink? Go to the bathroom? It doesn’t matter. What matters was that when he got back, he got some more stuff from the drawer and positioned himself behind C. C knew immediately what was going on, and moved a bit more upright, but still above me. His face was still right in front of mine, so I could see every detail of how his face scrunched up as B entered him, and then how he spread his eyes open wide as his friend started thrusting away. His erection, which had eased of a bit during all the lazy cuddling, was back almost instantly. I felt it brush against my arm a few times as I started to play with myself. While they were doing their thing I awkwardly snuck out from under them and sat down on the chair to enjoy the spectacle. Eventually the two changed position, with B lying down and C fucking him. At that point I moved over to them, alternating between kissing C and blowing B. From there we eventually moved back into the big pile of alternating positions.

My first time fucking two men started with me already on hands and knees at the end of the bed, giving B a blowjob. C had been lying next to his friend, kissing him, but now rolled off and disappeared from my view. Suddenly I felt a hand on my ass, and another between my legs, slightly re-positioning me. Then, of course, there suddenly was something else between my legs as well. C started fucking me doggy style, and within moments I had lost my blowjob-rhythm. Try as I might, the movement from behind and my gasps of pleasure prevented me from getting anything useful done. Even when B sat up on his knees in front of me. His cock was in me, and occasionally my rocking body would cause my lips to go up and down it, but you couldn’t really call it a blowjob anymore.

We were in that position when the two exchanged some words I couldn’t quite hear, and suddenly both drew back. I let out an indignant squeal over the sudden departure of penises from my body, which made them laugh. C told me to “just wait a minute” and laid down on the bed, gesturing me to sit on top of him. I crawled over and with one or two fumbling attempts was sitting on top of him, his penis once again inside me. I had only moved up and down a handful of times when I felt C’s hand on my should, pushing me forward. I did, locking lips with C while I was down there anyway. While we were kissing, I felt B put something wet on my bum, and immediately knew what he was planning.

I’ve mentioned that anal isn’t really my favorite thing before, but the idea of two men fucking me did tremendously arouse me, so I had told B I would be willing to try it. There was another awkward moment, but before long the two men found their rhythm, and I experienced what it was like to be taken in each entrance. The hornyness of it all more than made up for the pain-in-the-ass factor, and for a few minutes I was in ecstasy… until the feeling from behind got waaaay to intense. We took a little break and then tried again later on the evening. I lasted a bit longer that time, though to this day I still can not manage anal for the period of time that those men can fuck each other…

At one point, I think while he was fucking me, B let out a tortured “Oh fuck, I’m close!” In a clumsy hurry I jumped of the bed, nearly booting C in the face in the process, and sat down on my knees. B positioned himself in front of me and with a handful (get it?) of strokes he finished himself, shooting his stuff all over my face… and the floor and wall behind me. We had just spend an entire evening alternating between fucking and relaxing, so you can imagine that it wasn’t a small orgasm. B sank into his chair, still panting. I gave him a quick kiss, then darted of to the bathroom mirror to inspect his handywork (get it?) I know a lot of girls who want to get rid of a facial as quickly as they can, but… I dunno. I like the look of it. Makes me feel kinky… C didn’t know that though, and followed me into the bathroom.

“You’re not going to get rid of that before I can took a look, are you?”

“Taking a look, is that all you want to do?”

We kissed again. A thick strand of cum was left running from his lips to his chin afterwards. With a giggle I put my hand on his penis and led him back into the bedroom. I laid on my back on the bed as he got another condom. The sex was quick and to the point. He shoved himself in me as deep as he could, eager for his orgasm. His friend’s semen hadn’t even dried on my face yet when he suddenly retreated, impatiently pulled the condom from his cock and moved over to me, already jerking off. He painted me with another few strand of cum, though in his haste most of it ended up on the pillows.

B rose from his chair, allowing the exhausted C to collapse into it. After some kissing and some silly playing with the liquid stuck to my face he shuffled over to the end of the bed. After all that I was pretty close to orgasm myself, so his fingers and tongue only needed a few moments before all my muscles tightened up for a second and I let out something between a gasp and a sigh.

The "standard sexdating script" has that weird "shall we?" moment at the beginning, but there is an equally weird moment near the end. One moment you are lying on a bed after sex, possibly with a face full of semen, the next someone is suddenly putting on their socks. It's better when you can just fall asleep together, but at this point I was still living with my parents, so I really had to get back home at some point. B, who was already at home, just got dressed, while C and I shared a shower. Afterwards we shared another drink and some small talk, but it is just a bit awkward to get back to normalcy after such an evening. Before long B drove me home again.

Despite the weird ending it had been a fantastic evening, and the days afterwards I kept flashing back to it, wanting to plan another meeting. But it turns out getting three people together at the same time is a lot harder than just two! It would be a few weeks before I saw B again, and even longer before I saw him and C at the same time. But don't feel bad for me. I think that having to wait like that was the catalyst that finally got me to meet up with other people through sexdating...
発行者 HannahHester
7年前
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