The Sex Student Prequel - How I met Frank (f/m) | 2016

Merry Christmas all (or Hanukkah or Holidays or whatever...)

Here is the prequel I promised... but please if you are just starting my series, don't start here... read this after part 5... this isn't the story I want you to start with, it's just... well... a messy hookup that led to more later...

INDEX:

part 1

part 2

part 3

part 4

part 5

Anyways...

The Prequel

aka How I Met Frank

This story begins on a mid October night. Amy and I were downing a bottle of wine we'd snuck into our room and watching some romantic drama movie on cable. A sex scene came along and Amy started giggling.

"What's so funny?"

"It's so badly faked... they didnt even really try to make it look real..."

I watched the scene, but I didn't get what she meant, and chalked it up to the wine talking... I just ignored it and kept watching the movie. Afterwards, and after all the wine was gone, Amy and I were talking, and we got onto sex again. I was embarrased talking about my sex life... mostly because I hadn't really had one. Amy though, a bit tipsy, kept digging, and I finally came out with how I'd never enjoyed sex, never had good sex and never done much beyond letting them stick their cocks in me.

Amy looked at me in a funny way, then went to her bedside table, got out a book, and tossed it on my bed. "You read that?" I picked it up, Shades of Grey, I'd heard of it but certainly never read it. I shook my head. Amy just smiled "Read it... oh you DO finger yourself don't you?"

I went red... yes of course i masturbated, but why was she asking me? "uhhh... yes... why are you asking me that?"

"Just making sure"

So the next few weeks I read Shades cover to cover. I fingered myself while reading some of it. Amy got me comfortable fingering myself when she was there (she'd been doing it openly while I was in the room since we moved in together, I never said anything about it cause I guess I got off hearing her get herself off...), and a couple times I read stuff out loud as we both fingered ourselves. After Christmas break I started reading stories online, getting horny reading about how other people have explored their sexuality. I talked to Amy more and she really opened up my eyes to the fact there was more out there than just guys wanting to get off in a girl's pussy or mouth.

Then she told me about Frank... Told me how she knew this guy that was patient, experienced and got off helping girls explore. She showed me a picture of him on her phone, and I wasn't turned off at all by it. She asked if i would like to meet him and after a couple days thought on it I told her to set it up.

It was just over a week later on a Saturday night. Amy and I went to this club downtown. Amy had arranged for us to get in even though we were underaged. She went up to the bouncer who knew her by name and he let us in without even looking at me twice, his eyes were on Amy's ass as we walked through the door. "How did you...?"

"Oh Rick and I have had some fun..." she giggled and we found a nice quiet table in a corner not too far from the bar. The dancefloor was on the otherside of the bar and where we were the music wasn't so loud you couldn't speak. We got a couple drinks and waited. Frank showed up just as we were finishing the first round. Frank bought us all drinks and we talked about various subjects. Amy and Frank were like old friends but Amy was trying to get him into conversation with me. Finally we got to sex. Amy then dropped me into it...

"Lilly here has never enjoyed sex"

I glared at Amy who just gave me a look of 'you know I'm right'... Frank sat for a moment pensively...

"Does sex hurt you?"

"No I just have never gotten much enjoyment out of it"

Frank got closer to me on the bench seat. "I'm sure you just have not had a good lover"

"Maybe... but I now there must be more to sex too?"

Frank looked at me quizically "There is much more to sex than anyone can ever experience... the question is how much do any of us wish to learn"

I nodded and looked at Amy who was sitting there looking bored and trying not to be the third wheel... "Why don't I leave you two alone... I'll see you later Lilly, don't wait up" and Amy left to find herself someone to have fun with.

I looked at Frank and kind of smiled nervously

"Amy seems to think you should show me how sex should be... or so she said"

Frank laughed outloud "Amy has always been very honest and upfront... but she is a good friend to have, you are lucky to have her as a roommate."

"You two have... uhhh... been together haven't you?"

"Yes Amy and I had a sexual relationship at one point, but we are just friends"

I nodded, though I didn't understand how that could be.

Frank looked at me and asked me the one questions I'd be expecting "Why don't you enjoy sex?"

I gulped a bit but got the nerve up to answer "I don't know really? I read and get told it feels good to have sex, to have a cock inside you, but it never felt like that to me, just... I dunno... kind of dull and sloppy."

"You DO need a good lover, sounds like you've only had inexperienced boys so far" He looked at me in a way no one ever had before. I felt his hand on my thigh then him slide it up and brush my pantyline with his thumb. "I could show you... will you let me make love to you tonight?"

I was shocked at his proposal... I'd just met him a couple hours before! His hand stayed high on my innner thigh and teased me. Now not only was he asking me to let him sleep with me, but my mind was actually close to screaming yes. My mind was just spinning and I don't know how but something in me made me blurt out "Yes".

Frank smiled, then kissed me properly. Our tongues met there as we sat in that dark corner of the club. I knew other people could see us but for the first time in a long time I didn't care what people thought. Frank took my hand and led me to the door out of the club. We went down the street to a hotel, Frank got us a room and we went up there. Right inside the door he kissed me again and his hands roamed my back. We took off our jackets and then he ran his hands over my shirt, my back, my shoulder and then to my breast. He squeezed it lightly as we continued to kiss.

He broke the kiss and led me to the bed. He pulled the hem of my shirt up and I let him pull it over my head, bareing my chest to him. He smiled and leaned down, sucking on each nipple in turn. He stopped and pulled his shirt off, then helped me take my skirt off. I was now only in my panties. He shucked his pants off and pulled me onto the bed with him.

We kissed and caressed, then he slipped a hand into my panties. I touched me and it felt so good. I reached down and took my panties off. My legs spread themselves and he fingered my kitty for quite awhile. He carefully slipped a finger inside a bit and finger fucked me. Then he pulled off his boxers and I saw his cock spring free, he was already hard. He looked at me and I nodded. He got off the bed, grabbed a condom from his pants pocket, put it on and got back between my legs.

He rubbed his cock up and down my slit then slipped it inside. It felt better than anyone had before. I could feel him thrusting in and out, and all the time it felt good, no good isn't fair, it felt pleasurable, it felt... amazing honestly. Like a revelation, I finally was feeling pleasure from being fucked and it was making want it more and more. I felt an orgasm coming, and it washed over me like a tidal wave. As i came down I felt him speed up...

"I'm.... I'm... ahhhhhhhh...."

I felt him tense up and I realised he was cumming inside me. He finished and carefully removed himself from me, excused himself to the bathroom and I heard the shower. I felt conflicted... I was happy but at the same time now the alcohol was wearing off and I realised I'd just fucked a guy I barely knew in a hotel room. Frank came back out and saw I was getting upset.

"Lilly, you are an amazing girl... if you'll let me I'd like to show you how great sex can be?"

"I uhhh... I dunno... I think I should go..." I got up to leave.

"Lilly, here..." He pulled his wallet from his pants and pulled out a card, it had his info on it "contact me please? One way or the other, or with questions... ok?"

I nodded, got dressed and left...

And that's the story of my first encounter with Frank...