I met here here on reddit, with my other name. She posted to r/amiugly. Being completely honest with you, I only intended to reach out to the girl for two reasons , first she was very cute and you could tell she was incredibly sad in her pictures, two because of that sad I really did only want to help her and guide her if she wanted it in life.

I will admit, I did notice a shirt she had on, and half covered the wording, that would unmask her to be in my home state.. this also endeared the girl to me. After much long conversation, I found out she was a virgin who had failed many times , including currently with a boy she was head over heels for, with guys and never got any attention accept a kiss in middle school. I found this to be really out of this world, because she was very cute, and was very easy to talk to via text, yet I couldn't find anything wrong with the girl. As we talked more and more I did let it slip we were in the same state, come to find out just a hours drive apart.

We chose to hang out, I was a bit shocked at this, while she did see my post history (all nsfw) she was ok with it and said "you do you" she honestly seemed more interested at the time in mentorship and friendship, which is what I wanted to offer.

It took one meeting to realize this girls issue, she was the most awkward, introverted, socially inept person I have ever met in my life. She could hardly look at me, let alone form full sentences when we first met. So much that I often felt I had to ask if she was ok, as if she was uncomfortable with our in person meet up (in public park) that I would leave no harm done and we would go back to texting. She would insist I stay longer, even seem sad when it was time for me to go, this went on for a few weeks, long huge books of text, very awkward in person meetings. Funny enough her "hugs" were a light touch of her hand to my arm.

It took her time but soon the in persons she would not leave my side and sit, or stand very close to me when we were out or in the parks alone. I gave her so many tips on how to get the attention of the boys she liked, she would fallow them but she must have had some kind of rep and a "strange girl" at school because they would never bite. She would show me out fits in text, and I would help her pick out styles that would compliment her figure. Which was (as i know you want it ) Tall, for a girl, very slim, perfect small shoulders that complimented her smaller chest, to B cub breasts, small but not small enough you miss them (keep in mind i love small chested women) her stomach was flat, waist was even tinier then her little arms that I could put one hand around both wrists with ease. she had these deep waist curves that flowed to these lovely hips, another great feature of hers, prefect for grabbing up and holding on to. but unlike most uber skinny girls she had the most powerful legs, yes a gap, yes defined muscles, that you just would love to run your hands up and down all night on.

So, with her longer torso, and body type she wasn't good at picking out out fits (mostly baggy as hell name brand stuff) for her figure, I got her to show off a bit but she preferred to be covered up and would add things to the outfits I would recommend.

Some how, nothing.. I never could or did figure it out. I think it was her standoffishness, the fact that she would almost never directly look at you let alone answer a question. But once you get to know her, she is the sweetest little heart ever.. I think thats what threw me off, and lead me to our fateful night.

She kept asking about my ex's or other sexual partners, there were a few (the virgins) who she kept asking about, what they liked how things happened, what about them was attractive, I honestly thought it was her trying to figure out what she was doing wrong, and I am very wordy so I talk a lot and told her a lot. Somethings she harped on were some of the things I did and my preferences. One that was cute, was shaved pussy, I love it, so enjoy able to eat .. another thing she wanted to know about. so when I got the text "wow this feels good" I should have realized then that.. I might want to take a swing at her. At this point however I saw her as a student not a sexual being. I would have other sub missives while I talked to her and one hot summer night, while we were out walking by the lake she brought up one she often did.. the gf who loved to fuck in the car, not just fuck but be fingered hard more so while driving. She kept asking over and over, and about the "spots, and triggers" on a womans body, she wanted to know more.. also about the girls who had masterbated for me, so we talked more deeper about it.

:: messing around stuff starts here:::

while sitting by the shore that night, only the moon lighting us she sat on my lap, not uncommon at this point, and I showed her a demonstration of what those feelings might be, as I moved my hands along her shoulders and collar bone, brushing away the straps of her top and bra. She shivered so hard, I knew i had a neck girl.. so I played with her neck with my fingers, collar bone, shoulder blades, and gave her a bit of a deep massage.. she giggled and breathed heavy that she liked it, and it felt intense.

So I laughed, and showed her what my mouth could do. Her whole body clenched, as my tongue moved from her throat to deep where her neck meets her shoulders, my teeth digging in at the right moments, she made almost orgasmic moans.. I thought to my self how impossible it might be that she was sensitive this much but had rarely if ever fingered her self.
I moved my hand up her perfect stomach inside her top.. just caressing along her sides, and around to her back as I enjoyed her squirms on my lap. Taking momentary glances at her body writhing in my arms, her back arching I looked right at those perfect, but covered breasts.. I have honestly had thoughts about them from the day I first saw her pics she sent me with those outfits.. She had done so well to keep them concealed until now. When I slowly pulled away her top, to reveal this girl.. has a hot pink bra with purple lace lining.. I had my self a naughty girl, it made perfect sense if you look back to all the pics she sent me, the questions she would ask.. the awkward girl was the most naughty girl one could hope for just she had no way to express it. I moved my mouth down her chest, biting and sucking at her flesh as I went I had to have them, I love breasts and once I had the taste of her flesh in my mouth, my only option was to devour hers. I pulled her bra cups down with my teeth to reveal the most perfect bcup breast I have ever seen in my life, they were flawless. I felt her nervous heart going a mile a second, as I sunk my mouth into the one on the left, moving my tongued slowly at first, along each bit of flesh licking underside and up, all over kissing, biting, sucking and then the speed tongued on her nipples she then let out the deepest moan, that shocked me I didn't think she was capable of and shoved her hips back and down, thats when she felt it.

She jumped a bit, let out a soft "oh my god" with a full on deer in the head lights look in her soft blue eyes, she just stared at me. She was wanting to say something so bad but she couldn't get the words out, I pulled her back to my body, but not back to my hard cock that she had just grinded her tight little ass on, softly brushed her hair with one hand and fixed her cups with the other. "are you ok?, did you want to stop?" I asked I'll spare you her awkward replies' and stammer, she had never felt a cock before, and didn't think it was going to be big. I tired not to laugh and brushed her hair sweetly, then holding her by her face, pulled her in for a soft sweet kiss. The rest of the night no matter where we went was full of me touching her, kissing her lips.. something she became obsessed with after that first kiss.

She would text me almost all night after that, asking more questions, showing me her underwear she had on that night after I complimented it, and her breasts.. then I learned, she covered them up so much as she was embarrassed about their size, which i loved. She sheepishly asked, in the most round about way possible, if we would do it again. I was free the next night, but not day so I went and picked her up, this time found a different place , more secluded and we just sat and once again, I enjoyed her from the waist up.. a few times letting a finger trace the inside of her panties, just to remind her I wanted other things too. back on her neck she would squirm and writhe, but this time would make her ass dig right into my lap, she smiled , almost wickedly when she felt it. So I pushed it back at her. After we got something to eat, we were driving , I was going to take her back home but she begged to go on a drive, she pulled my hand from the wheel and wrapped her body around it, something a previous girl had done before.. I found it odd that she was doing this, as she almost never would start touching me first, except for a hug, or to sit on my lap. She then pulled my hand between her legs. I looked over and she was smiling, and I knew she was trying to recreate one of my stories, where I fingered my ex on the way to a dinner in the car. I told her did she really want this? That her being a virgin this might not feel good for her first time fingering.. she agreed. I pulled over in a dark parking lot, pulled her on to my lap, leggings and panties all the way off.. She did shave her pussy and it looked so fucking good, these bois had no idea what they were missing.

She was very tight and winced at my single index finger, I moved as slow as possible using her body for ques. I told her ot take off her top. I enjoyed her naked body, she did as she was told.. I devoured her perfect tits, her stomach, her lips as I slow fingered her and showed her every part of her pussy that mattered, her clit with my palm, her inside spots with my finger she squirmed her hips moving around.. I know what she wanted to feel.. I made her work for it.

then I thrusted into her and she got the biggest smile, I was insanely hard. I couldn't help my self her cute little mousey face just lighting up like that i started to choke her and move a bit faster, working her spots, her clit , she desperately tried to push her ass against the hard cock she thirsted for.. thats when her eyes lit up, huge as a full moon her chest turned beat red, her stomach tightened, I pulled her into me "its ok, let it happen" I kissed her deeply.. her first orgasm, as I would later learn had her cumming all over my car seats and pants. I held her as close as I could, caressing her naked body. I love this part, when the girl finds her climax, when I give it to her and get to hold her sweet little shape in my big hands. More awkward chatter from her, it was so cute, lots of wow's and oh my god's and what was that, over and over. she sadly was too afraid to do another but then said.. she had never seen a cock in real life, never sucked one. .. who was I to deny my student?

She stared at it for a bit, she marveled and felt afraid to touch so I took her hand had her stroke it, showing her how. sitting in the passenger seat she almost couldn't believe, again the awkward girl words flying out, she kept talking , so nervous it was cute when I said to her, "do you want a taste?" she just looked at me.. I slowly took her head, over the center console, and down to my cock, "its ok, just take a little kiss"

She kissed it and pulled back.. let out the cutest scream. It took some coaching but she got the top in her mouth.. then my sweet socially broken student learned to suck her first cock. I taught her just the basics, tongue movement, use of her hand, nothing really advanced. she never could get too much of it in her mouth and focused on the top a lot! oy that was really like edging for me. I recall thinking she will never be able to make me cum, I'll have to do a late night call.. But she was determined , she kept up her awkward talking, she would pause and giggle each time she made me feel really good and I vocalized it.

Then right when I was about to tell her to stop as this went on for almost a half hour, her going at it, stopping just long enough to delay it, and then going back. She did edge the fuck out of me, she while looking down whispered something I almost couldn't hear.

It took awhile but she had said "I want you to cum" I would find out later in our text chat that week, she had been looking into my nsfw and had this fantasy to get me to cum, more so on her face.. that would happen later.

I told her a few ways that might happen, and said to hold still.. I started going at her mouth, while she stroked the lower half of my cock, if she gaged, and she did, I would pull back a bit fucking her cute lil face, while doing so, I felt her pussy, rubbed it, fingered the edges, she really started to open up, I am not sure I could have fit two fingers but i think to of hers would fit. She looked soo good going at it, on my cock the moon light lighting up her pale skin, when I came, it shocked her.. she pulled back, got a good mouth full and chest full as well. bit on her face. She didn't stop smiling as I cleaned her off. I did make her eat what she spilled.

I dressed her top, but not the bottom of her, and put my jacket over her lap, I felt she had opened up enough playing with me she might be able to take it, so changing her hip angle, I held her pussy tight as I fingered her on the drive home. She said it did hurt, which I was afraid it would, but she loved it.. wanted it again.

This time, when I dropped her off, she passionately and deeply kissed me like crazy. I was shocked, didn't see that coming. Later that night, she wanted to video call, I talked her though cumming again. A bit frustrated as it wasn't as deep, she kept saying how I had to do it again for her, I promised I would.. she talked about how afraid she was of cock that is much much bigger going inside her, I told her that her first time will be ok, it will hurt a bit but it will be alright in the end you just have to take it easy and with the right person.. she got this angry determined face, "no" she said, "it has to be you"...