The sex student, part 7 (f/M) | 2016

Haaaaaappppppyyyyy 2015 everyone!

Well if you missed a couple this is part 7... the 8th lesson. Here's the links to the previous parts in case you need to catch up ;)

Index

part 7

I really hope you are all still enjoying these. The response to the last couple was a bit disappointing, but it was over the holidays so I'll chalk it up to that.

As always I really do like hearing from you all and sharing things that aren't in the stories. I'm very open to questions and comments so please feel free!

And now, Part 7...

The next week was busy to begin with but by Wednesday had gotten very dull. I had no lectures or even important class work to do. Amy too was bored. We spent Thursday cleaning up our dorm. We sat down Thursday night to a movie Amy got. It wasn't very interesting and I started playing games on my phone. Amy wasn't going to stand for that so started digging...

"So you and Frank... you having fun?"

"Yea..."

"You like getting creampied?"

"What is...?"

"When he cums inside you..."

"Oh that... yea I do actually."

"Ha, taken him in your ass yet?"

"Uhhh... no... but he will soon..." I told her about the envelopes.

"Interesting... surprised he didn't yet though..."

"I don't know if I want to try it..."

"You don't know until you try Lilly... I think you'll be surprised."

We traded a few more barbs about my sex life but we moved on to other subjects. Friday came and went and my mind was now turning round and round on anal. It was a wet cold Saturday that week. I got to Frank's and he let me in quickly, but with no comment. I took a longer than normal shower to warm up. I dried off carefully then went to find Frank. He was in the bedroom sitting on the bed waiting for me, in his robe like usual.

"Come in Lilly... sit down" he patted the bed next to him. I sat myself down and he immediately ran a hand down my thigh and up the inside cupping a finger on my slit but not rubbing it or penetrating me at all. He kissed me long an carefully, but kept my tongue out of his mouth and avoided long touching of our tongues, keeping me from getting too into it. Just as I started to get aroused he broke the kiss and took his hand off me totally.

"Now it's time to pick your lesson for today" and he held up the last 2 envelopes. I gulped mentally, 50/50 chance that the envelope I'd choose would be that one that scared me so... I took a deep breath and took the right one. I opened it carefully and tugged the small card out. The 4 letters that so frightened me appeared... Anal.

"Frank I don't know about..."

But he held up a finger... "Lilly, I won't force you to do anything, but I really do ask that you try anal... It won't be bad and if after the first part of this lesson you want to stop we will, ok?"

I nodded.

"Good... now what scares you so much about this? You've come so far, I can't believe it's a fear of pain along?"

I shook my head "Well, a bit but not only that, remember my parents are doctors... the stories they've told for years around the dinner table, my mother especially talking about what she'd had to open someone up to remove from their rectum... I don't know if i can move beyond those mental images it and into getting pleasure from it."

"I see... well I won't be putting anything up into you that isn't safe to use that way. Every toy we will use will have a stop of some kind to keep it from going in too far... actually lets begin with showing you a couple..."

He got up and brought a bag over to the bed, there were some brand new toys inside.

He pulled out the first, a long red dildo looking one with a flat piece at the bottom and a ring to pull on "Simple anal toy... nothing strange about it" He gave it to me, it still reeked of new plastic. It was softer than my other dildos but still very long. I laid it down on the bed next to me.

He pulled out the next, this one was black, short and fat, pointy at one end a bit. "Butt plug... this one is fairly small... but not what we will start with..." He gave it to me again to play with. It was hard rubber but smaller than I'd expected, smaller at it's biggest than 3 of my fingers.

He pulled out another, this one longer and... looked like a dildo with balls on it "Here we are... these are Anal beads... well modern ones anyway. The old ones were more like balls connected with strings, these are much safer and easier to clean... but I do have" and he reached back into the bag and pulled out something that looked like a strange string of pearls "an old style one as well... these are also called Thai beads sometimes." He gave me both to touch. The modern one was rubbery plastic and over a foot long with 8 'balls' on it. The old style one was about two feet of cord, 8 white balls and fine string about 2" long between each with a longer tail and a long metal rod, the stop I realized. I looked back at Frank who was smiling at me. "The old style is more entertaining to watch being used, but for today we will concentrate on just getting you started."

He took the toys back and only kept the dildo and the plastic beads out, he put the other 2 back into a bag and put them aside. Then he brought over some lube and wipes. He sat back down next to me.

"Still scared Lilly?"

"A little... but those aren't really that bad looking... not sure about the plug but the other 3 look... ok?"

"You will either love or hate a buttplug being in, but we won't worry about that until you are more used to having something up your ass ok?"

I nodded once

"Good, alright before we use toys though, I'm going to start off easy... so I'd like you to get up on all fours"

I looked at him for a moment then got onto my knees in the middle of the bed, I looked over my shoulder at him and he motioned me down. I got down on all fours. I felt very vulnerable, knowing that Frank was going to touch me where I'd never really wanted to be touched before, but my mind kept saying at the same time that I really wanted him to. I was surprised when I felt his tongue on my clit, he started licking me hard and well. I started getting very aroused, his tongue felt so good, but then it moved down, licking along my labia, probing in between. Just as I got used to that i felt a touch between my ass cheeks, a finger rubbing along the ridge towards my sphincter... and then touching it oh so lightly. My heart jumped and i felt an electric feeling jump through my loins. The finger rubbed up a little then back down again, this time pressing into my nub, again I felt a strange feeling. The finger starter to massage into my nub, I felt the lube make it start getting in, and then without any effort I felt it pop in. Now it burned a little... my body telling my brain it needed to do what came naturally... but my mind resisted.

"Are you ok Lilly?"

"Yes... it's... weird... but it's ok" It wasn't a lie, it didn't hurt. The burning was getting better now...

"Good, just relax as much as you can, you are doing fine"

"Ok..."

He started to move his finger in deeper, then pulling it back. The burning got worse again then better until it was almost gone. I felt a strange cold clammy feeling on my skin but at the same time my clit was throbbing and I felt very aroused. Frank then slipped another finger up against my sphincter and pressed it in. The burning came back for a moment as it stretched to accommodate the new digit but then better than. Now Frank began really finger fucking my ass. He stopped licking me and I felt him move into position behind me. He started to twist his fingers around a bit as he moved them in and out. Then he stopped with them all the way inside me.

Next thing I felt was a cold dollop of lube being put above my little nub, then the fingers came out and I felt something new... it was one of the toys. Frank pushed it into me and it went in easily. It was the straight dildo, and it was in about as far as his finger had been. Frank left it there and I felt my body pushing it out but something stopped it.

"Good Lilly... you are doing very well, how does this feel?"

"Ok..." I felt a bit winded, but still my body was fighting itself over if it liked it or hated it...

"I'm going to use this on you for a few minutes, just try to get used to the feeling..."

He began moving the dildo in and out. I felt it getting deeper inside me. I had no idea how much of it was in me but I knew it was much deeper than his fingers had gotten. Then I felt the base against me, it was all the way in. Instead of pulling it back Frank twisted it and shook it a little inside me. I felt it move my insides around. Then he let go... and the toy stayed where it was, in fact I felt my body pull the base against my skin.

"Feel that Lilly? You have about a foot of toy inside you... lets see..." He traced down my stomach with his finger... "about this deep" he pushed his finger into a point near my belly button. "You can take much more... are you ready to try that?"

My mind spun again... it felt weird, but I wanted more... It wasn't the feelings I expected at all, more intense feelings than I'd bargained on an almost no pain at all. "Yes" I blurted out from somewhere.

Frank patted my ass, then I felt him pulling the dildo out slowly. Pushing it in a little at times until I felt it come out and my sphincter suddenly squeeze itself closed. Then I felt his fingers on either side of my hole, pushing my cheeks apart and holding me open a tiny bit. Another application of lube followed, then I felt him start to put the anal bead toy into me... I felt the first ball push in and my sphincter shrink in between the knobs. Then a second... and third... the feeling of them moving in was actually not unpleasant. Four, then five, then six... each one feeling my ass stretching then squeezing it in deeper. The seventh went in then I felt a sharp feeling inside... something wasn't right.

"Frank stop... something... sharp... inside"

"That's ok Lilly, that's just as deep as it will go today... I'll pull it back one" I felt the knob open me back up and come out... the sharp feeling stopped instantly. "Feel better now?"

"Yes..."

"Good, now enjoy this..."

I felt him change positions and realized he was laying under me now, then his tongue was on me again. He licked my clit and... all I can say is wow happened. I felt a sudden shocking pleasure which just built but then seemed to stop at that thing sticking out my ass. Again and again as he licked me, and my normal pleasure was building through it too. He kept up his tongue flicking and I came hard, but it felt different. I could feel my ass try to shrink around the toy. Frank kept going and I came again... then again... and AGAIN... four times in very short sequence. My legs felt like rubber, I was shaking. Frank was holding my hips and kept licking my clit... It was too much, I felt like I had just swam 20 miles, my whole body was quaking but Frank kept going, I tried to say something but words wouldn't come, so I came a fifth time and I just collapsed forward and rolled onto my side. Frank pulled his head out from under me (I couldn't of stayed off him), I lay on my side panting, my whole body was buzzing.

I felt shift behind me and kiss me, then I don't remember anything until I found myself still lying there under a blanket. The toy was out of me and I felt ok. I sat up and felt a bit light headed. Frank wasn't there but there was a note on the bedside table to find him when I was ready. I looked at the clock, 11pm. I got up and found my strength again.

I walked out of the bedroom, Frank was watching TV on the sofa in the living room. I could feel lube between my ass cheeks as I walked. Frank smiled as he saw me.

"Hey there, feel ok?"

"No... i feel amazing"

Frank pulled me to him and kissed my stomach.

"I pushed you a little too far I'm sorry... how many times did you cum?"

"Five I think..."

"Five!? Lilly, I only licked you for 15 minutes... I've never... Five really?"

I nodded.

"Well... no wonder you collapsed on me... I've never given anyone five orgasms in one go before. I mean I know I made you cum four times when I went down on you before, but that took almost twice as long." He looked up at me. "Do you want to keep going, or call it quits for the week?"

"Lets keep going... I feel ok now, really."

He pulled me down and kissed me on the lips. "Ok then, lets go shower"

We went and showered. Frank washed me all over, but carefully washed between my ass cheeks and even pushed into my nub a little. He rinsed me carefully then held me in a kiss. He realized he hadn't cum yet at all, hadn't even had me touch his cock. I reached down to do that and felt him hard already. I looked up into his face and found me looking at me. I got down on my knees there in the shower and sucked him. He didn't last long but just as he was going to cum he pulled himself back and sprayed cum all over my wet neck and chin. I rinsed it off and we got out of the shower and dried ourselves off.

Frank led me back to the bedroom and had me get on my back in the middle of the bed. He started to suck on my nipples then ran a finger along my slit. My arousal started again, and I was happy I wasn't totally drained. Frank kissed me and we held it for a long time, our tongues swirling and sliding around each other.

"Well, there is one big thing left for today's lesson."

I looked at him quizzically, I could think that there was more for him to do to me for a moment then it suddenly came to me. Sex, he hadn't fucked me yet. "You mean you want to fuck my ass?"

"Yes Lilly, I very much do"

"Ok i guess..."

"Good, now a couple things, today I will wear a condom for this... and I will probably not finish inside you but we will see"

I nodded... I looked down and he was already sporting another hard on.

"Lay flat on your stomach Lilly... I need to get you ready again..."

I lay down flat. I felt a finger probing my ass again, then lube. It burned again, but that got better quickly. I felt the finger pull out then heard Frank put the condom on. I felt him get over me and felt his weight on my back.

"Are you ready Lilly?"

"Yes"

I felt him put his cock at my nub, then push. It actually hurt a little and it slipped out and up. He did it again and I felt it start to go in, then with a pop his cockhead was inside me. I felt him sink into me and then his balls against my ass. Then he pulled back up and back in slowly. It felt strange but was starting to feel good. And I could feel my clit rubbing the bed a little. He started to thrust faster and faster until he was at a pace similar to normal fucking. I started to actually like the feeling, not the straight pleasure like being fucked, but something else. I don't know how long Frank kept it up but he finally started to lose strength and slow down panting.

"I have to stop..." and he pulled out and got off me.

He lay there on the bed, his cock twitching... I got an idea... "Can't I ride it that way?"

Frank looked at me shocked. "You can, but that's really tough I wasn't going to as you to do that even the second lesson on this... are you sure?"

I nodded and got over him. I took his cock base in my finger and got into position.

"Ok easy, lean back as much as you can... just feel my cock at the opening of your ass"

I felt his cockhead hit that point and let myself down, I felt it push into me... it didn't feel right and I tried to change the angle a little. It got in a bit more and then I slid down suddenly. It was all the way in but it didn't feel good in me. I tried to ride a bit but only took about 4 thrust... "No... I doesn't feel right..." I pulled off and it came out.

"It's ok Lilly... thank you for trying, you aren't ready to feel the right position yet, and it does have to be right."

I nodded and lay down... "But I want you to finish... can I fuck you, if you take the condom off?"

"No Lilly, that's not safe, you could get all kinds of infections from that, maybe after we start cleansing you before, but not tonight"

"Ok, what can I do?"

He considered a moment, then pulled the condom off and started to stroke himself. "I will just stroke myself off... and cum on your ass."

I smiled and got up on all fours watching him next to me. As he stroked himself I fingered my clit a little and my kitty. I found I was soaking wet still. Frank smiled as he saw me doing myself. He got behind me and I felt his cock between my ass cheeks, then I felt the warm splat of cum there. Frank plopped down next to me and smiled at me.

"Lets go shower Lilly"

We went and showered again. He rinsed the cum and lube out of my ass, then cleaned his cock very carefully. We dried and went back to the bedroom. We lay down again side by side. I looked at the clock is was 2:30am now. I wasn't tired, but could tell Frank was. I wanted to be fucked so much though I just moved in and sucked his soft cock into my mouth. He got hard quickly. I stopped sucking, then got into position straddling him again, this time I guided him into my vag and started riding him. I kept a slow pace up that was really good for me. Frank just lay there and watched me, his arms outstretched flat on the bed. I just enjoyed the feeling of his cock in me, I felt my own orgasm coming and wanted it badly. I sped up and let it wash over me. After the previous events it was a bit weak feeling but it still felt so nice. I felt Frank stiffen and realized he was close. I rode him hard and fast, feeling my tits rolling as I did, I could only imagine the erotic sight Frank was seeing. I kept going, I wanted to please him...

"Oh Lilly... " and I felt him start to twitch inside me, then that warm flush. I stopped and pushed myself down onto him. I felt him relax and his cock was still. I carefully pulled off him and let the cum run out onto him. He pulled me forward and we kissed.

I lay next to him and he fell asleep. I turned the light off and lay there. I must of drifted off, when I came to there was light outside, Frank was still there. I just lay on my back snoozing, remembering the last day. Frank woke up and touched me. I rolled over to face him and we kissed. He had morning wood and I tried to stroke it, it shooed my hand away and shook his head. Instead he led me to the bathroom and into the shower. We repeated the golden play of my holding his cock as he pissed. When he was done we showered. I was a mess down there but didn't care. I got everything washed out while Frank watched. When I finished he shut the shower off and we kissed again.

"You can go Lilly... but I have much more to teach you I now know for sure"

He kissed me again and left. I got dressed, left and went back to my dorm. Amy was there when I arrived watching some TV.

"Well, another overnight? And you don't look like you survived a riot this time... oh let me guess you pulled the anal card?"

I smirked at her "Yea..."

"Aaaaand?"

"And... I didn't hate it."

She smiled and went back to her TV show. I changed, grabbed some food, then just settled down for a quiet Sunday.

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The sex student, part 7 (f/M) | 2016