She let [M]e jerk off onto her [f]ace. | 2016

Allie and I worked together years ago at an amusement park. I was 22ish and working as an assistant manager; she was 17 (don't worry, nothing sexual happened until she turned 18) and worked as a cashier at the snack bar (separate departments, but honestly I didn't give a shit about "inappropriate workplace relationships". I was 22 and this was just a miserable summer job.). She was pretty average looking, and a bit mousy, so she didn't always get noticed. There was at least one slutty girl who worked with her (I'm not a slut shamer or a judger, but let's call a spade a spade) who got all the attention from the sex-craved teenage employees, so Allie tended to get overlooked. I heard through some whispers that she had actually slept around a bit, but it stayed on the DL. The rumor was that she was a "dead fish" in bed (their words). Between my typical lustiness fueled by a few-month dry spell, the challenge of breaking her out of her "dead fish" reputation, and my life-long attraction to the shy, mousy girls, let's just say I set my sights on Allie.

I started talking with her. I didn't flirt too heavily (partly because she was still a few weeks away from 18 and partly because I had occasional second thoughts about becoming Eskimo brothers with some of the dudes I worked with), but we became friends and I started learning little bits of information about her. For example, her phone was sitting next to her at the cash register while she was ringing up a customer one time and I noticed a text come through. She never changed that setting where the texts show up on the lock screen, so I could see what it said. I forget the exact verbiage, but basically it was a guy talking about anal, and I could tell from context that she had said she would be willing to try it. Obviously that caught my attention.

Flash forward a month or so. She's turned 18, and I convinced her to come over to my apartment to watch Archer (and that's how we get ants!). We ended up making out, but nothing more. I wound up leaving my job at the amusement park and I found a pretty steady fuckbuddy, so things died off. About 6 months later, somehow we start talking again. I honestly don't remember the pretext, but we met at a bar (even though she couldn't drink) and then she came over to my place. We fucked. It was nothing fantastic, but it was alright. I could see what the other guys meant by "dead fish" — she was pretty quiet and submissive in bed. However, I took that as a challenge, and by the end of the night, I'd made her feel comfortable enough to be a little more vocal and tell me what she liked. Like I said, the sex wasn't the best, but it wasn't the worst. The one thing I really remember is how she was so small I was almost afraid to hurt her (she's really petite). Her pussy was extremely tight, but she kept asking me to fuck her harder and deeper. A few times I could tell it was hurting her so I would ease off. She would take a few seconds to catch her breath, and then she was right back to asking for it harder and deeper. That's the attitude. We only fucked two or three times, but after each time, she would tell me how sore she was and how she had a hard time walking the next day; she told me she absolutely loved that feeling. She literally just wanted to get railed. What a fucking champ.

Before our first time, she told me that she was allergic to latex, and there was no way in hell I was going to ride her bareback, so I offered to track down some of those lambskin/sheepskin things. She literally told me not to bother — she would just deal with the irritation from the latex the next day. I remember being incredibly turned on by the fact that she wanted my dick so bad, she was willing to overlook an allergy. That and the fact that she got incredibly wet made her the most eager cock-craver I'd met at that point in my life (foreshadowing!), and that more than made up for her average looks and quiet tendencies in bed.

We both eventually fell out of touch. Until ~2 years later, when she contacts me out of the blue. She basically tells me how she's in a relationship that's pretty unfulfilling (emotionally, sexually, you name it) and the guy sounds like kind of a douche. She tells me that she misses my cock, and that his doesn't measure up. Maybe she's stroking my ego, but I don't care. I'm not hung like a horse, but I'm definitely above average. I've been described as "big" by more than one girl. The conversation steers away from sex, and we decide to meet up for drinks and to catch up (she's finally old enough to actually drink at this bar). I was in a steady relationship, so I knew I shouldn't, but you can guess which one of my heads won that argument. We met up, had a few drinks, and talked. Against my brain's better judgement, I invited her back to my place so we could "talk without all this noise" (because Chili's is such a fucking metal concert during the lunch hour, amiright?). Obviously things escalated, but they did so in a deliciously slow pace. She was never against anything, but you could tell that she was apprehensive, and that made it so much hotter. Through some other bullshit excuse we move from the couch to my bed. As a "joke", I whipped my dick out. She's openly staring, but also obviously conflicted about what to do. She laughs, but doesn't make a move. I start playing with it to try and keep it semi-erect without being all the way hard (you know, gotta play it cool, even when your cock is hanging out of your pants), all the while continuing on a normal conversation with her. She says something about how much guys love when a girl makes eye contact during a blow job, and I tell her I haven't experienced that in such a long time because my current gf doesn't go down on me (a lie, but in for a penny, in for a pound, right?). Couldn't she get between my legs, put her face next to my exposed (and now semi-erect) dick, and look up at me with those brown doe eyes? Again, she's apprehensive and conflicted, but you can tell she wants to. She finally agrees with the condition that I don't trick her and smack her with my dick while she's down there... Sheesh, what kind of guy does she think I am?

I continued escalating things, and she continued going along with it. Always putting up a resistant attitude, but never taking my multiple offers to back down and never saying no to anything I asked. She was obviously really in to it, but I think it relieved her conscience to act like I was the initiator. Whatever, I'll bear that burden happily. Next came "Why don't you just hold it so you can remember what it feels like", then came "Why don't you just pop the head in your mouth for a few seconds? Not a blowjob, just for old time's sake." Then finally, "Can't you show me these newfound blowjob skills you've bragged about? I just want to know what all the hype is about." I remember it being funny because when she first started blowing me, it was only on the condition that I put a pillow over my face so that I couldn't watch her. Apparently she was self-conscious. Again, whatever. After a minute or two I took the pillow away and watched her every move, and what do you know, she didn't object. Like I said, she did all these little things that apparently helped her justify the whole situation.

I was actually a little disappointed because she talked a lot of talk about her mad blowjob game, but it was decent at best. I remember thinking that I would never get off that way, so I told her to lie back and I straddled her chest. Oh yeah, her shirt and bra came off at some point, so now I'm sitting just under her exposed tits. I remember the padded bra... yeah, a 21 year old wearing a padded bra. Just further illustrates her self-consciousness issues. I started jerking off, but I started to feel a little bad when her squirms revealed how horny she was and I realized that she hadn't had any attention. I'm really not as much of an asshole as this story would have you believe (I think it was just a turn-on to play out this dominant character with her that I normally don't exhibit), so I unbuckled her short shorts and snaked my hand in to her panties. I will never forget how wet she was. The word "soaked" literally doesn't do the situation justice. Even before I parted her lips, I could feel her dripping. I spent about 10 seconds on her clit, and then slipped two fingers inside her. It was weird because she was still really tight, but she was so wet that there was hardly any resistance. I curved my fingers towards her belly button and found her spot. Her eyes scrunched up, and I swear it took maybe 45 seconds before she was arching her back up towards my ass (I'm still straddling her chest) and mouthing who-knows-what obscenities silently. She came hard. I mean hard. I'm not trying to dwell on this or tout my own skills (because honestly, all did was finger her). It's just so vivid in my memory. I think it was the fact that her current boyfriend couldn't get her off (so she hadn't had an orgasm at someone else's hands in months) combined with the taboo nature of the whole scenario that culminated in this really intense orgasm. When she came down, we both laughed a little at how quickly and how hard she had just climaxed. My dick was now as hard as it'd ever been, and pointing directly at her face. I started jerking off, and it didn't take long before I told her I was close. "Not in my hair," she said. I'm normally an oozer not a shooter, so I didn't think that would be a problem. Oops.

In retrospect, I tend to squirt my cum when I'm really turned on, but I wasn't exactly thinking logically. The first wave of my orgasm hit, and a strand of cum shot across her face, landing half on her forehead and half on her hair. Fortunately, the rest shot all over her closed eyes, nose and lips. I'm not like the other guys in this sub — I honestly have no idea how many ropes of my cum were jettisoned towards her eager face. All I know is that it was more cum that I usually shoot, and her face was respectably splattered. We caught our breath, I gave her a hand towel from the bathroom, and we cleaned ourselves up. She hung around for about 10 minutes trying to make small talk, which was awkward because I suddenly remembered that I had a serious girlfriend and the post-orgasm guilt started setting in. Being the true champ that she was, she never complained about me cumming in her hair, even though she went directly from my place to her shift as a hostess at a local Mexican restaurant. I distinctly remember her sarcastically thanking me for the fact that she would have to spend the next 8 hours working (although "swimming" is probably a more appropriate gerund here) in soaking wet panties.

We didn't see each other again. We talked a little more, and she complained about the worsening state of her relationship. He got a job on the other side of the country, and she followed him. I think she thought it would help to save things between them. Right before she left, she told me that she lived out one of her fantasies to have a threesome with two strangers at a party. She used to tell me how much she wanted to try anal — an act we never attempted due to her petite anatomy and my not-quite-petite anatomy — and how she really wanted to try DP. The funny thing is that the two guys at the party were too cock-shy to DP her, or even to spit-roast her for that matter, so they ended up just fucking her missionary style one after the other. Silly kids. She moved away with her boyfriend, who eventually proposed to her. She lost her phone and her contacts, and I decided it was probably healthiest not to send her my number for her new phone.

However, these days when I need a little help getting over the edge, replaying her whole-body orgasm followed shortly by her whole-face cum catch never fails me.