Posting the story of that night.
[03:44] Christopher: sorry to hear that you’re joining me in the metropolis of masturbation.
[03:48] Christopher: well, if it’s any consolation, I just finished finger-fucking my own ass while masturbating
[03:48] Christopher: (which I’ve started doing much much more often since you did it to me)
[03:50] Wilhelmina: hfuireshfsjuews
[03:50] Wilhelmina: i’m flattered
[03:50] Wilhelmina: but thank you for raising the temperature THAT bit more
So let me tell you a little bit about Christopher. I met Christopher sophomore fall. He was sitting quietly – reading – and wearing an interesting-looking shirt.
And I went up and asked him what he was reading.
That is important because I don’t approach people randomly like that. Ever.
He’s in one of my classes, and we start hanging out. I hear that he has a long-distance gf he’s very serious about, but that didn’t stop him sleeping around. I’m single at that point, and looking pretty desperately to date someone, but mentally write him off because he has a long distance gf. We start to get pretty close. Despite attempts to escape it, I have a huge crush on him. One night we’re randomly hanging out in the basement of that nerdy frat. Both pretty tipsy. He’s pensive because he is in love with his gf but needs/wants to have sex with other people too, doesn’t know what to do, and asks my (!) advice. His comments make me feel extremely frustrated, and I half-jokingly threaten to start throwing things at him if he continues along those lines.
To cut a long story short – he comes home with me and we have sex for the first time that night. I didn’t even have to do much persuading - at all. We’re friends-with-benefits for the rest of the term.
Summer rolls around. Obviously, the friends-with-benefits thing stops; I assume for good.
About a week after I’m already on my exchange, we’re both tipsy, horny, and online.
[03:51] Wilhelmina: so tell me
[03:51] Wilhelmina: how do you feel about strap ons
[03:51] Christopher: right now, I’d say, lube me up fuck me hard
[03:51] Wilhelmina: shit
[03:51] Wilhelmina: if i were there i totally would
[03:52] Christopher: how much would you enjoy that?
[03:53] Wilhelmina: i would love it.
Ironically, I had left a bag of my stuff in his room, due to last minute packing and storage being closed. A bag of stuff – including my newly-bought strap-on and harness. I tell him this, and:
[03:53] Christopher: hahaha, I am seriously tempted to use it right now
[03:53] Wilhelmina: do it
Whoa. Hot. I assume he’s going to just go off and use it and come back – after which I would demand details of his little experiment. But I’m wrong – he wants me to screw him with it – over the internet. He also tells me that he’s been masturbating to memories of certain… previous activities:
[04:05] Christopher: you riding me while fingering me
[04:05] Christopher: 69ing together
[04:05] Christopher: fucking you from multiple positions and angles
[04:06] Christopher: you, sucking, biting, squeezing, cumming
[04:11] Wilhelmina: if i were there right now
[04:11] Wilhelmina: i would probably
[04:11] Christopher: wil, I’m using your KY and masturbating as we speak
[04:12] Wilhelmina: i would probably blindfold you
[04:12] Wilhelmina: push you onto all fours
[04:12] Wilhelmina: tie your wrists to the headboard
[04:12] Wilhelmina: shove your face into the mattress
[04:12] Christopher: please, yess
[04:13] Wilhelmina: maybe spank you a little
[04:13] Wilhelmina: see if one of your belts were lying around somewhere
[04:13] Christopher: (it is, I kinda tore my pants off recently)
[04:13] Wilhelmina: and then i’d lube you up
[04:13] Wilhelmina: like i did
[04:13] Wilhelmina: those times before
[04:14] Wilhelmina: and then
[04:14] Wilhelmina: pull the harness on
[04:14] Wilhelmina: and
[04:14] Christopher: (wow, you have gotten really assertive, and it’s hot as hell)
[04:15] Wilhelmina: AND.
[04:16] Wilhelmina: fuck you slow and hard
[04:16] Christopher: …oh god
[04:16] Christopher: you’d better be masturbating too
[04:17] Wilhelmina: i kick your legs apart and move really slowly….
[04:17] Wilhelmina: allll the way out and
[04:17] Wilhelmina: then
[04:17] Wilhelmina: alll the way back in again
[04:17] Wilhelmina: (i’m actually not, i’m paranoid of my roommate, but i really want to…)
[04:17] Christopher: do it!
[04:17] Christopher: masturbate while your roommate is sleeping
[04:17] Wilhelmina: (she’s not asleepnfirehtgsiurehgt)
[04:17] Wilhelmina: ( = why i’m paranoid)
[04:19] Christopher: wil, if you reach into your panties and masturbate right now, I’ll put your strapon into my ass right now
How could I have said no to that? I do what he tells me to. I rub myself – I’m already wet. Christopher keeps his word and describes sliding the dildo into himself… saying that it’s bigger than anything he’d ever tried before, but amazing. I’m impressed that he can manage to jerk off, screw himself with a dildo, and type all at the same time – and his typing is eloquent as well. I’m significantly less eloquent.
[04:20] Wilhelmina: mmm
[04:20] Wilhelmina: imagine
[04:20] Wilhelmina: me
[04:20] Wilhelmina: fucking you
[04:20] Wilhelmina: hard.
[04:22] Christopher: I’m imagining you fucking me
[04:25] Christopher: I have been playing with my ass a ton more since you finger-fucked it
[04:25] Wilhelmina: heh…. i’m glad
[04:25] Christopher: oh god, your dick feels SO AMAZING in me
[04:27] Christopher: i’m busy stroking myself up and down my cock and sliding the head of your cock into my ass
[04:30] Wilhelmina: i love(d) being inside you
[04:30] Wilhelmina: so warm and tight and intense
[04:31] Christopher: oh shit, i love it when you’re inside me
[04:31] Christopher: it hurts and feels like heaven at the same time
[04:32] Wilhelmina: i’m pounding you aren’t i.
[04:32] Christopher: yes
[04:33] Wilhelmina: i’m lifting your leg up
[04:33] Wilhelmina: spreading oyur legs
[04:33] Wilhelmina: wide
[04:33] Wilhelmina: if the light is on i can see everything
[04:34] Christopher: the lamp is on, you can see every detail sliding into me
[04:34] Wilhelmina: it’s kind of mesmerizing
[04:36] Christopher: it’s wild feeling my ass slide around your dick
I had been ‘fucking him from the side’ until then, but he asks if he can ride me. I say yes. Wanted him to all along – except I had been taking things too realistically. In real life he never could have done it. I’m 5’1″ – pretty tiny – and while he’s no football player (I can’t abide football players), he’s substantially tall and strong enough to carry and maneuver me with little effort.
[04:43] Christopher: put your fingers inside yourself
[04:44] Wilhelmina: my middle one’s in
[04:44] Christopher: and your clit?
[04:45] Wilhelmina: still rubbing
[04:45] Wilhelmina: feels good
[04:45] Wilhelmina: closing eyes
[04:45] Wilhelmina: now and again
The ridiculous thing is that my roommate is talking to me the whole time this is happening. I try to respond to her, and sound neutral enough but extremely out of it.
[04:47] Wilhelmina: raise yourself up so
[04:47] Wilhelmina: the head is almost out then
[04:47] Wilhelmina: slam back down
[04:48] Christopher: oh, fuccccckkkkkkkkkkkkkkkkkkk
[04:48] Christopher: that almost made me cum
[04:50] Christopher: I can’t wait to be fucked by you
[04:51] Christopher: and fuck you so hard myself
[04:51] Wilhelmina: can’t wait.
[04:51] Wilhelmina: i’m almost coming
[04:51] Wilhelmina: almost
[04:51] Wilhelmina: …
[04:52] Wilhelmina: god i want to feel your ass convulse around me
[04:52] Christopher: me too– every time you pump into me I’m gasping
[04:52] Christopher: and every time you pull out i’m almost wimpering with pleasure
[05:07] Christopher: do you think your roommate caught on to the fact that you were cumming while remotely fucking a guy on another continent?
[05:07] Wilhelmina: uh, no
[05:07] Wilhelmina: she probably just thought i was being strange
[05:07] Wilhelmina: which is nothing new
[05:07] Christopher: hahaha
[05:10] Christopher: okay, virtual snuggling time
[05:10] Wilhelmina: (snuggle)
[05:45] Christopher: man, that was sudden and very sexy
The wonderful thing about being friends-with-benefits with Christopher was that he’s so versatile. He was the first guy to let me finger-fuck him. It was amazing. Before him, I hadn’t been with a guy I could even mention the topic to. But I found it easy to bring it up with Christopher – just like it was easy to bring up anything. When I asked if he had done it before, all he said was something about the prostate existing and that stimulating it was extremely pleasurable. The first time I did it to him, he gasped and almost came. For me, it was… warm, and tight, and intense. After that it became a fairly common occurence between us. I finger-fucked him while I blew him, while I rode him; we did it to each other at the same time…
I confessed to him as well that it was one of my fantasies to screw a guy with a strap-on. Penis envy? Not really. Beyond this, I feel no desire whatsoever to be male, or to have a penis. But penetrating somebody else with something more than just fingers is… amazingly trippy. And a strap-on is great and all, but I would love to actually feel everything. And I don’t mean I want to feel a vibe throbbing against my clit while I’m screwing someone… no. I want to be able to have a penis, and feel all the heat and tightness and softness. But that’s not going to happen anytime soon. I like being a woman, thank you very much.
F (despite being straight) says that she has the same desire, i.e. to have a penis in order to penetrate a person during sex, but when we talked about finger-fucking and screwing a man she said she wouldn’t be up for it. Ironic, because she’s the one who dresses like a guy sometimes and acts more ‘masculine’ – while I look and act like a femmy flower-child.
I’m so happy that Christopher said that he couldn’t wait to have sex with me again. And I’m happy that I helped introduce a new kink into his life. It also looks like that I’m going to introduce him to another kink after I get back to College. Seriously – can’t wait.
Yes, he’s still with his girlfriend. He’s still in love with her. He’s still (potentially) sleeping with me behind her back. Except that she lives far, far away and has no way of knowing about what we’re doing. And Christopher’s feelings towards me are strictly platonic and playful-sexual.
Believe me, I had hoped for a lot more. Once. I hoped that he would fall for me and leave his girlfriend to go out with me. I hoped that he would fall for me and want to be with us both at the same time. I hoped he would fall for me and… do nothing about it except tell me, just… I wanted him to fall for me.
Buuut… he didn’t. We stayed friends. We kept having sex.
Do I think such behavior is okay? No, not really. I’d never encourage someone to sleep with a person behind their significant others’ back… but at the same time, if I knew of someone who did that I wouldn’t necessarily judge them badly either.
Do I feel guilty? Honestly? No, I don’t. Does that make me a bad person? Some would say so. But, so far, I haven’t hurt anyone. Yet.
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