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#Mature #Teen #Virgin
By Courtney
In all my 43 years I’ve seen a lot of kids come through here and it’s the same things every year. I work at the local highschool as the librarian and have been at this school for nearly 15 years now. As much as I wanted to, I never found a husband, so instead I have resigned myself to the modest role I occupy and try to stay happy. In my line of work, I overhear so many conversations from different students that can’t keep quiet. So many think I’m just an old bitch for telling them to be quiet all the time, but truth is I secretly like to listen in. I’ve learned more about them through the years than a spy for the CIA. Another bonus is I can spend my time reading books, which is something I’ve loved doing since I was a little girl. Over this school year though, I’ve noticed one student in particular that I’ve been following in secret very closely. He’s a senior now but I’ve watched him over the last three years go from a shy, yet optimistic young man to an even more reserved man with no hope in his eye. I’ve seen him get rejected by all his crushes and make him give up on women almost entirely. He was never bullied, but didn’t have a lot of friends either. I talked to him a bit like I do with other students but he is unaware of the extent of my knowledge of him.
So last week he was telling me about a girl in the year behind that he wanted to ask out. I encouraged him as any teacher should, but today I see him walking in sad and lonely looking.
“Hey there Mike, what’s the matter?” I asked him. I sat down next to him at the table in a secluded corner of the library.
“I was walking up to Britney to ask her out like you said, but before I could get up to her she got in the car with some other guy.” he answered.
“Are you sure it wasn’t her father, you may still have a chance.” I told him.
“No, he was early 20’s looking. But they kissed for a solid minute before he drove away. She’s 17, what’s she doing with a man like that anyway?” he asked. I could hear the sadness in his voice.
“It’s ok, it’s normal to go through rejection and heartbreak a lot before you find the right one, that just makes the one who says yes that much more special. You’re a handsome young man, and you haven’t even left for college yet. I’m sure you’ll be getting girls left and right once you’re there!” I said as I rubbed his shoulders in consolation.
“Really? Well, Mrs. Courtney, that’s the most thoughtful thing anyone’s ever said to me, your husband must really love you. I know I would.” he said back.
“Actually, it’s just Ms. I’m not married yet.” I confessed.
“There’s no way. How hasn’t anyone gone after you yet?” he asked me.
“Who knows, I guess I’m just unlucky. So instead I sit here and read books all day.” I told him. I must admit, this is the most flirting I’ve done in years, and it was enough to make me so excited down below. But Mike was still a student, and I was a teacher. It couldn’t happen even if I wanted it to.
“What kinda books do you like Ms. Courtney?” he asked.
“Romance is my favorite, however with the time I’ve had here I’ve read pretty much everything in here.” I told him.
“You must know a lot then, no wonder you give such good advice.” Mike said.
“I know things that would rock your world if only you were a little older. Forgive me for being blunt, but we share the same problem and I think we can help each other. Only we can’t tell anyone about it ok?” I asked as my breathing hastened as I looked him in the eye.
“Wh– What do you mean? Are you saying–?” he stammered.
“Yes Mike. I can give you the confidence to have any woman you want, and I’ll finally get the ‘romance’ i crave for real for once. Come to my office, no one will bother us there…” I said standing up and strutting away making sure he saw my ass clearly. As we walked to my office, I was almost light-headed from how turned on I was right now. I haven’t had a boyfriend in 7 years, and my last hookup was nearly 3 years ago. Mike was 18 so legally it’s ok from that point of view, but the teacher/student angle still complicated things. But I didn’t care anymore. I was feral for cock. I shut the door and locked it, closing the blinds on the window beside it, and turned to Mike who sat in the chair in front of my desk.
He started to speak, about to ask what was going to happen. But I put my finger over his lips as I walked around the chair. I bent over as I stood in front of him, letting him pear down my top to see my soft, round tits.
“You like ’em? You want a better view?” I asked before ripping open my blouse to show my boobs contained only by a thin, black-lace bra. His face went red, and his cock about burst through his jeans. I got on my knees between his legs and opened his zipper, removing his pants and underwear. Exposing his rock solid cock. It wasn’t the biggest, but he was only 18 and I haven’t gotten any in years so I was more than happy to see it. Part of the books I read were “sexual instruction” books that I studied inside and out, and combined with my romance novels, I was going to polish this kids knob like he never thought possible.
“Ms. Courtney…” he murmured before I silenced him again with my lips around his cock head. I used every bit of my mouth and tongue on him, his virgin cock. He could hardly breath as I sucked him off. I almost thought he was crying before I went for a deep throat and he actually did. He lasted maybe two minutes tops before he blew his load in my mouth. I felt honored I could make him cum so fast, and that I could taste and swallow his virgin load. But he wasn’t done in here yet. Fuck no. As his cock went limp, I sucked and stroked it harder to bring it back to life. When he was ready to go again I stood up, and removed my dress, pushing my bare ass out at him as it fell around my ankles. I wasn’t wearing panties under my dress, and my bra had been removed long ago.
Now I put one leg over him and sat down, straddling his lap with my hips, lowering my pussy down on his tower. As I lowered myself down, the grip I had was intense. I might as well be a virgin again with how tight I was while he stretched me open. All the while I held his head in my arm pulling his face against my boobs while fucking him deep. I kissed the top of his head while he worked into a rhythm with me, fucking like lovers. My boobs bouncing in his face made his cock harder, which made me fuck him more passionately, which only made my boobs bounce more. Neither of us said words, just heavy breathing, grunts, and those squealing noises that I haven’t heard myself make in so long. With one hand, he gripped my ass tightly to slam down on his cock harder, and with the other around my back, he held my tits against his face as he sucked one after the other. It was so sexy to e so desired by a man again that my pussy was leaking cum with his every thrust.
I just shook my head rapidly up and down while crying as I hit my first orgasm in 5 years. All from a boy who was 13 when I had my last one. I was drowning his cock in a puddle of squirt from fucking him. He tapped me on the shoulder and I looked him in the eyes for a moment. He wanted to change positions but wasn’t yet strong enough to pick me up. “How do you want me?” I panted as I rode his cock.
“On your back, on the floor. Now.” he ordered.
I did as he said, and spread my legs. He got between them and re-entered my pussy but now he was in control of the fucking, and he fucked me with a speed and desperation even I couldn’t match. He was fucking the sorrow and rejection of seeing all his crushes get taken by other men out on my pussy, and I wanted all of it. His youthful energy wore me out, but I couldn’t tell him to stop. I needed to be fucked good and hard. I didn’t care if the principal walked in, I’d still keep fucking him. I pulled him down to me, and we were locked together, with my legs firmly around his ass now. He looked at me as he ravaged my cunt and I knew he was close, without saying anything. Then in an instant his eyes rolled back and I knew it was happening. He slammed down deep into my pussy with one final thrust as his cock erupted into my soft wet hole. I was in tears as I begged for it all.
“CHRIST FUCK ME YES!” I moaned as he let loose his entire ballsack into my womb. The cum he shot into me was swimming upstream from the torrent of squirt I shot out at it from my pussy as we orgasmed together. After we finished, he laid on my love pillows as we caught our breath. We kissed deeply as he asked if this was a one time thing.
“Keep it a secret, but I’m ok with this becoming regular…” I told him. He put his clothes on and left the office as the bell rung for next period. He missed a class, but the experience he gained would be life changing. I sat in my office rubbing my clit to what just happened. Even the thought of it gave me another orgasm. I should’ve been fucking these boys for years!
———-
I just wanted to say that this is to t he day, one year since my first ever story I posted here! Thanks for everyone who reads and gets off on them, I’ll continue as long as I can. Hopefully I’ve improved since then but I’m not ready to quit just yet! See you all in the next one…
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By Courtney
#Mature #Teen #Virgin
