Pleasuring My Timid Friend

In college US History class, I saw a classmate, Clair, sitting at a corner looking withdrawn. In the next few weeks, I constantly saw her with her head down and never socializing with adjacent students nor raising her hand to ask or answer questions. Halfway in the semester, we got partnered to write the course midterm paper. I hoped we could socialize more to possibly become friends and maybe lovers if things go well, but Clair kept acting shy, just talking to or texting me on my phone or coming to my home for paper related issues. When she came one day, I took her to my room, made her sit on a chair, and sat facing her.

She could tell I was mad as I asked why she was acting like this. She fidgeted and hesitantly said she had a bad childhood as many students picked on her for various reasons, the school staff rarely helped after she reported their bullying, and as a result, she hardly made any friends. Life at home was not better.

Her parents punished her harshly if she got anything under an A in any class test or project. I said her life will just worsen unless she changes for the better. She said she does not want to change, fearing it would backfire. I held her hand and assured her I could help her improve her life in many ways. She froze for a few seconds, then agreed. I was excited, then said I wanted to do one thing that would make us both happy and that is to kiss and lick all over her body, give her oral sex, and finger her. She was shocked and said no one did this to her before, but agreed to this after I said I would not help her unless she concurred.

We held hands and lip locked, then I kissed and nibbled her neck and chin, saying to not be afraid as she stood up. I took off her shirt and kissed all over her stomach and sides, then her vagina through her pants. I told her to about face, which she did, then kissed both of her arms and down her smooth back as I took off her pants. I sniffed her buttocks, my favorite part of any woman's body, then grabbed, kissed and licked all over both cheeks. She shut her eyes and moaned softly, proving she enjoyed it and I did also for obvious reasons. I sat in front of her, kissing her pussy through her panties as she held my head moaning.

I stood up as we held each other's torsos and lip-locked. She sat on the seat as I sat on the floor in front of her. I kissed both of her feet and up her legs and thighs, then up her stomach and sides to her lips. We lip-locked. I took her bra off. She looked shocked. I rubbed her breasts while kissing and nibbling her neck and chin, then kissed and sucked her breasts and nipples. She closed her eyes in joy, clearly liking it.

I kissed down her stomach and sides to her panties, then fondled her vagina over it as she giggled. I went down on her as she moaned loudly and held her head, clearly loving getting oral for the first time. I did that for a bit longer, then fingered her as she panted heavily in joy. She at a point grabbed my face and kissed me as I fingered her harder. I kept doing that as she held my head to her chest. We fell to the floor.

We lay on the floor with her in only a pair of panties and a blanket over us. I had my arms around her torso and head on her chest. She fondled my head and said she loved what I did to her. I said I did too, then asked if she was ready to give me oral. She said she was, but looked at the clock and realized she had to go home, thus she assured me she would do that next time. She got up and we kissed goodbye. She got dressed and left. She gave me oral in our next sex session at her home, but I had a kinky idea for our third.

In my room, I told her I wanted to tie her hands to a ceiling nude and kiss and lick her body fully as she begged me to quit and let her go. She was shocked, but knowing how popular BDSM is, said yes in hopes she could make new friends. She undressed fully. I handcuffed each of her hand to a chain attached to the ceiling. We lip-locked as I held her face and ran my hands down her torso. I kissed and nibbled her neck and chin and felt her breasts, then kissed and sucked them and her nipples while fondling her vagina and feeling her butt. She said she was getting scared. I kissed down her stomach and sides, then sat on the floor in front of her, gave her oral and held her breasts. I told her to put her legs on my shoulders. She did.

I grabbed her ass and gave her more oral. She told me to stop and she had the urge to pee, but did not. I kissed down her legs and thighs to her feet, then sucked her toes and fingered her. She said she was trying bad to not pee and wanted to go home. I sat behind her, fingered her pussy, grabbed her breasts and kissed and licked her entire ass. She said I was making her uncomfortable and it harder for her to not pee.

I licked between her ass cheeks, spanked them and sucked her anus. I fingered it while kissing up her back until I stood behind her. I then had anal sex, kissed and nibbled her neck, shoulders and arms and felt her breasts and pussy. She peed on my hand. She apologized, but I said I loved it as I stood in front of her and said to wrap her legs around me. She did and we had intercourse as I grabbed her butt and breasts. She whispered she loved doing this. I said I was proud and we lip-locked until it was time for her to leave.