+3 Finger-F*cking the Friend, and Other College Stories [LR]

Three stories recounting the last bits of fun college has in store for NightRoller…

So this week we see a continuation of the story begun in the “Drunk Friend’s Kiss” post. But before that, enjoy a few other logs of my adventures, which I needlessly delayed.

Edit: I added some more details to the first story, which may be useful for beginners, and added a follow-up to the last, which had an interesting sequence of events following the first night…

Busty Kinky Spontaneous Fun

I mentioned this briefly in the first few lines of this forum post (requires an account), for reference for myself and anyone else keeping track (mostly myself).

This story occurred with a busty quarter-Filipina, a very nice girl. She was surprised when I gave a back massage and fingered her after I came and generally cared about giving her a good time. Apparently most of her experiences in the past told her guys are selfish and just care about getting their d*ck wet, whereas some guys want to give the girl the best time she’s ever had in bed and care about whether she’s enjoying it (you’re reading the blog of one now), whether it’s meant as a retention strategy, to stoke one’s ego, from outright enjoying giving the girl pleasure, or genuinely caring for the girl.

We matched on Tinder a couple weeks ago, and when she asked for a dance lesson and “tonight” (the night of the day we matched) was among the options she was free, I knew it was a decent shot, and it was probably better to strike while she was open and spontaneous… though she wasn’t very sexual in text and not super responsive with the usual logistics for arriving. But she did come out and arrive, I gave her a kiss next to my window and then the clothes came off.

She did get her personal dance lesson. “The sexy fucker who cares”. I want that to be my new title. Aimed to give her the mindset of “we’re on the same team” from Andy instead of combativeness, which also seemed to surprise her. Empathy is too rare in men’s toolkits. Told me she originally intended to meet me for just a dance lesson but underestimated how hot I’d be in person (haha!)

She was not as energetic as some, but active in a way that reminds me somewhat of Seductress Girl and turned me on enough to host her at my place for a round 2. Shy, but a bit more sexually forward once she was comfortable, and helped to remove my belt and wanted to suck my c*ck. Liked the taste of my dick, apparently. I’d put her at a 6 or 6.5. Really cute, loved sex, kinky, a switch, loved being “a good girl” for me, but was also fun to talk to. She didn’t like her boobs, ironically. This is the kind of girl I’d be fine with “settling” for for a few months/couple years, if only I wasn’t leaving the area soon. Hope to see her again, but she’s mostly ghosted since we met, so it may not work out despite living relatively close.

I had another post-it-note of thoughts about her, but don’t have it handy as I type this, so I’ll update this post later.

Update:

From her, and by conglomerating the feedback I’ve received from other girls, I must have an above-average d*ck, or at least a strongly above-average ability to use it. Never taken out the tape measure when I was at my hardest, but apparently I’m “thick” (when she told me this, I thought she meant my thighs, because of my bulk phase, but she clarified it was referring to my genitals).

I used a lot of “you’re thinking [thing] / you’re like [overexaggerated simplification of how I perceive or guess about her]” in the interaction. Cold reading is a skill. I think I am improving on that front.

I wrote down that this meeting was a “Lay Up”, in how it was practically handed to me on a silver platter. There were a bunch of small places where I could have f*cked up in the past, or would have just been neutral (awkward but fumbling through it), but where I was smooth as creamy peanut butter in this situation.

I hit many, many of her firsts (first time using a toy, first time orgasming with a partner, etc.), enough that I was nervous of overwhelming her. I think I set the bar higher for the next guys she sees! Sadly, will not likely see her again, as she ghosted–except for a couple butt-dials when my notifications were off at night.


Cute “Big” and Kind Girl Slips Past My Defenses

A lay with a bigger girl, small enough to slip past my still-improving filter of left-swiping on bigger girls (I keep getting told by RedPillDad (who I would link, but his old site is private) to step up the quality of the girls I see, and I’m trying little by little), but she was cute enough, nice enough, and sufficiently interesting in person that I didn’t turn down the opportunity despite her being quite big in real life. I got to try flogging and proper spanking for the first time and gave her a few firsts too. Good times, good experiences overall. She wasn’t needy or clingy either, which helped me maintain interest while we hung out. I could tell she wanted to keep seeing me, but after 1 date afterwards, I turned down the attention while recognizing that her size bored/disinterested me (it was difficult to get very deep in her, for instance).

One thing I’ve observed from seeing so many bigger girls is that they tend to have a higher pain tolerance and take more stimulation to get turned on, on average, so grabbing, scratching, biting, spanking, and similar are more required to cause the same reaction/pleasure/orgasm as a more healthy-bodied girl.


The Friend Wants To Be Desired/Seduced

As promised, the continuation of “Drunk Friend’s Kiss”. But first, let’s set the scene of that day:

I had a coffee date earlier that morning with an unrelated girl I matched with on Tinder, who I brought back to my room similar to the first girl in this post to see if she was open to makeouts and more with the premise that we’d listen to each others’ music, but she kept distance from me the whole time and I had a difficult time turning things away from the logical. Very little eye contact too, despite even coming into my room. As a last-ditch effort, I verbalized that I was nervous and wanted to kiss her, and she asserted a no-kissing-on-first-dates rule. I replied that I didn’t believe in arbitrary rules for dates, but said I would respect her for it. Better move in the future: instead of agreeing to her arbitrary line, challenge her on it verbally. Is it something she really believes in, or is it just a screen to find the guys who are confident enough to make a move? She said she’d “think about” whether she wanted a next date, which means, ~3/4 of the time, a delayed no.

I had a date planned with someone from Tinder who was horny and wanted to see me, but kept coming up with excuses (which she would discard if I made her horny again) why she couldn’t do our date later that day’s evening, such as getting banged by a guy the previous evening and regretting it (which she did after we set up our date a week ago for this day—if you’re not f*cking her, somebody is; as RedQuest says, “why not have that person be me?“). I’d turned it around over text a few times, but she finally said that morning that “she couldn’t make it” and I simply replied with “I understand”, accepting it wasn’t worth the effort to try to make her fit in my tight schedule.

So I was primed to kiss someone pretty on this day, maybe a little needy. But focused. And when the friend who kissed me drunk excited-texted me 4 or 5 messages in a row, I knew that there was a chance we could get into things.

I kept my expectations low and hopes high.

She wanted me to make the move, and signs pointed to her wanting me to make one, but in no way was any of it explicit; in that regard it was not at all like the dates I’ve had where it’s “on”; she also kept shifting the topic to all sorts of random things whenever we would have quiet and have eye contact, or when things turned sexual. She was nervous too, it turned out.

She was definitely thinking about us kissing, or more; she was open to coming to my room, which we hadn’t done before during this year (most of the time, we go to her room to chill, and don’t ever stay more than a minute in my room, but she was happy to bring her chair to mine). She interpreted my actions as being “disappointed” when she suggested we go out to get dinner at a nearby restaurant and assured me we’d be back soon enough (I was about 50/50 on whether that was just flowery words or an actual promise). She mentioned on our dinner that she was feeling unsure about how to go about trying non-monogamy options, which her current main love interest was most interested in. Funny how, if you’re a girl and interested in a guy, you tend to fall under his frame on what is “okay” vs. “not okay”, and casual sex with others is now “okay”.

Once again looking back with the benefit of hindsight, she wanted to be made to do things, and I wanted to make sure I didn’t overstep and push things too far and ruin our friendship by her losing respect, which led to a few hours of talking (plus dinner) before we even started kissing, much less getting undressed. She also revealed later once we were losing clothes and I was handling objections that she worried that by opening sexually to me, that I would see her differently. (To be honest, my view on her changed even before she kissed me drunk, as I began to recognize female psychology applied to her and she wasn’t just an exception. So at this point, my views are settled and sex didn’t change my opinion of her.)

Funnily, during our conversation, when I finally got closer and was approaching the topic and possibility of us kissing, she expressed to me that she interpreted my change in the past couple years as happening after she told me what her sexual preferences are and that she liked some BDSM-related stuff. Honey, no, sad to say but I’ve been reading up on what most girls like, but nice for you to think I thought of you while doing it. She wants the story to be about her, to be swept off her feet by a guy making effort to woo her, coming from being a super “weird”, nerdy, unattractive guy who “wasn’t her type” and was “too skinny”. She emphasized all of those things, all of those reasons why I wasn’t a good fit for her, and I don’t know if it was just a defense to try to deter me or to deter herself, but it didn’t stop us from kissing or getting intimate later that evening.

She was very nervous and wanted to know that I really wanted her and wasn’t just saying it or pretending it. She wanted to know I would genuinely like to f*ck her, because she has nerves and insecurities about how she looks and doesn’t believe others when they say positive stuff (but still wants to hear the positive things all the time to stoke her ego).

Once again, she very much desires to be triumphantly right, and was very disappointed when I rated her kissing as mediocre. So it goes.

Cute tits, pretty face, thinner than she lets herself think, and squirms all over when close to coming–reminded me even more of Seductress girl than the big-breasted girl at the top of this post.

The one boundary she set was not putting my d*ck in, which I followed, but lots of finger f*cking and several orgasms. She claimed that getting f*cked by two different new guys in the same 7-day period would be too much (I forgot that it’s been longer than a week, and should have mentioned that… once her forebrain would have said “okay sure” her hindbrain would have been delighted to give in, from my point of view).

I learned a lot from her because we’ve been friends for some time, so there’s some things we can say more easily to each other and curious questions were not rebuffed.

In the end, I didn’t jerk off or get jerked off, but partly because she’s proud about having “not had sex” (in her mind), I want to be contrarian and claim it counts anyway, whether I put my d in or not. By how tight and buoyant and well-lubed my fingers felt inside her, I don’t doubt she’d feel fantastic if I do f*ck her in the time that we’re still in the same area…

She mentioned that she was surprised I was so good in bed, when I asked how I stacked up. My boasts are not unfounded; I’ve learned that much. She’s not very experienced, so the guy she’s now in love with (who’s half-across the globe right now) seemed fantastic compared to the loser guy she was engaged with (who likes videogames and is too engineer-type to think about sex as a skill), but any guy with above-average skills would be able to show her a fantastic time if they got through her filter.

I’m going to continue to keep her as a friend, because we know each other so well, but when the occasion arises, if she’s also open to getting her mind blown, I’m not opposed to being friends with a little extra fun in the mix. I may even have my d*ck in her at some point. Either way, we got to learn a lot about each other by the end of the night that we’d never discussed before, due to the veil of being friends before (and, she mentioned, she was more interested in hearing about all the girls I was seeing… she loved when I mentioned that how she squirmed reminded me of Seductress Girl, who I occasionally miss and remember fondly).

The saga may continue…

Update: And so it does

Firstly, for the next three nights she joined me in my bedroom. As I recall them, the second night (out of the total of 4), she came over with the pretense of wanting another back massage because “when she woke up the previous morning she’d been ‘not sore’ for the first time since she was a kid”. Back massages are a serious skill. Once again, we kissed, I used my arms and gave her a wild night on my fingers, but not my d*ck. She said this time was even better than the previous, and that I was now actually better than the guys she’d played with before. More cuddling, more interesting and useful talk and questions. Oh, and I might have tied her up with some rope, just for fun. I gave her a different kind of orgasm too–one where she felt like instead of forcing it and letting it happen, it forced itself over her.

The third night I forget what reason she came over, I may have invited her to just chill spontaneously that night or we might have planned it. Either way, it was similar to the previous night in how it flowed, with even less rough patches from either of us, and we made it an awesome time. I actually started to feel tired at one point in my arms from the consecutive days’ exertions, but I didn’t feel the need to slow down before she was exhausted. We talked more, she mentioned she worried that if we had sex she didn’t want it to affect our relationship as friends who talk about sex, and worried also that I would be so good she’d want to leave her current pseudo-boyfriend. I don’t want a relationship with her either beyond friends-who-also-happen-to-bang-the-shit-out-of-each-other, so I understood the complaint. She also squirted for the first time this night, which was cool.

All the previous nights I’d made fairly plain that I wanted to put my d*ck inside her, and all three nights she’d rebuffed me. I didn’t expect this 4th night to go any different, but I knew it was the last night we’d be in town before we left, and so I was a bit more aggressive. It bears knowing that this whole time, I had kept myself from masturbating/orgasming, in case I might be called to do my duty, but I was not yet. I knew she liked aggression and being liked. Half of me ran on instinct, and half of me ran on seduction when I was more forward with her this time, diving for the kiss and telling her I really wanted to have sex. She asked how bad, and I replied a 9. It progressed and wasn’t a certain thing, until about 6-10 minutes in, when she told me to grab a condom. At that point, it was like “okay, it’s happening“, and we did several positions. She likes control play, being in total control or being totally dominated, with little in between, so it was quite fun. I did notice I’d grown a little tired of her kisses, though; they were still sub-par from what I prefer/am used to. And we parted on good terms, as usual, got to talk about all sorts of stuff beyond the 4th wall that I can’t usually talk frankly about because of the magic of the moment and not knowing the other person well enough. I could understand a bit of where those who say “be friends first before you get married” are coming from, though I still refuse to take their advice.

And with that, as I told RedQuest, I am now “a guy who will, if the opportunity arises, seduce his female friends, and teach them how to be better in bed while also listening to their feedback.”

And now, we make plans to rendezvous this summer, despite the distance, and we’ll see how things continue then. We’ve sexted a couple of times in the interim.


This brings the overall count to 28 more-or-less lovely encounters in the first twelve months since I lost my virginity. Now things will slow down for a time, while I move away from a college campus and out into the middle of f*cking nowhere.

I don’t want to repeat the effort it took (<< see the last few lays in that post) just to be able to get a few more sub-par interactions or instances of car s*x. It did help my texting slightly to get used to using more overt language and become comfortable identifying what worked to text girls back when I used the sub-par apps, but this summer I’ll have some other priorities besides getting my d*ck wet… until I board a plane for Europe (requires an account).

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