I (F) was a mean cocktease to the guy I was tutoring | 2016

NOTE: I never inappropriately touched the boy I was tutoring, I did not fuck him, nor did I ever want to. I’m a lesbian and I don’t swing that way at all. I wanted to get that out of the way before I started.

Right after college, I had moved in to this suburban neighborhood after I got my job (I work in I.T). There was a family of three next door and I was good friends with the mother. Their son, let’s call him Alex, was in high school and was doing badly at math. His mother had asked me if I could tutor him after I got back from work. I accepted.

Lessons started to go well. And since it’s relevant to the story, I will just add that I’m not that bad-looking. My chest is a bit on the curvier side and I always make it a point to hide it. The problem is that most shirts and t-shirts become quite tight and send up emphasizing them even more. It’s a battle I stopped fighting long ago and now usually sport bulky loose dresses even if they make me look fat. The loose fitting often made my movement quite restrictive as my girls would get a bit too bouncy and cleavage being visible when leaning over even a little bit was inevitable.

So anyway, the tuitions took place at my place. It right after I came back from work and I was usually in my office clothes: a white shirt, a pencil skirt, black stockings, and my hair tied up in a bun. He’d take occasional glances at my chest or my ass when he thought I wasn’t looking. Not that I minded. I couldn’t exactly blame the guy. I thought it was adorable how his face would get all flustered and would stutter. There were times when after the class was over, he would say he couldn’t get up right away because his leg fell asleep. He’d often scurry away quickly, after having untucked his t-shirt, trying to hide his boner. I found it hilarious. There was one time when I decided to toy with him a little. Right as he reached the door, I told him I needed to talk to him about the uncovered syllabus and called him back. He reluctantly turned and the t-shirt was too short to hide his erection. I asked him what was in his pants, pointing at the bulge. He mumbled that it was a bar of Snickers. He looked a bit scared and I thought it’d be funny to mess with him a little.

“Oh. Can you show it to me?”

“Why?”

“Cause I’d like a taste.”

“No..”

“Well, that’s not very nice, is it?”

I stepped closer and said: “Then I guess I’m just gonna have to put my hand down your pants and take it out myself.” I swear that he was fucking trembling. I told him to relax and that I was joking. Said I wasn’t hungry.

I’d fuck with his head like this quite a bit, mostly because I found it fun. Just a few examples because I don’t want this to be too long:

1) “Is it hard? Let me know if I’m making it too hard.” - Talking about a math problem.

2) I play badminton and my shuttlecock was busted. I showed up at his place in my uniform: a mini-skirt and a t-shirt. He was the only one home. Walked right past him and into his room. He followed. I said, “I want your cock.” He rarely played, so I assumed it was still rigid and not worn down. “Is your cock still stiff? I need to practice my strokes.” I even offered to take him to the badminton court: “You don’t play with it that often. I have half a mind to make you come.” Not one word. He didn’t say a damn thing. I quickly clarified I needed his shuttlecock. He pointed at the bottom drawer. I was in a bit of a hurry, so I quickly bent over and searched the drawer until I found it. I hadn’t realized at the time that he could probably see my ass. I think I was wearing only a thong as it’s not restrictive while playing.

A week before exams: His dad’s mother had passed away and the parents had to go to another city. Alex was to stay at my place for the week as he needed to study and give his exams. The night before they left, the parents had gone out for some work. I had assumed that Alex went with them too.

So I have this habit of trying on various lingerie and dresses and sometimes taking selfies when I’m alone. Honestly, it makes me feel sexy. The various grandma dresses I have to wear are quite depressing. That’s one of the main reasons I do it. The only other time I can truly let go is when I’m on vacation with my girlfriend. Anyway, it was around an hour of me just trying on different stuff, adjusting how my boobs look in various bras, and just goofing around a bit.

The next day, before the parents left, the mother tells me that Alex was home the previous night. I have to mention that we live in row houses like these and his bedroom is right next to mine. They’re very close together. The light in his room was off and I thought there was no one home. I had carelessly not drawn the curtains. I realized the little fucker must’ve been watching.

The next week while he was at my place, I was so mad that I blueballed the ever-living fuck out of him. I honestly had zero fucks to give about my attire at that point. Aerobics every morning and evening in a tank top and shorts, tight t-shirts, low-cut outfits. I didn’t give a fuck. He was sleeping on the couch and I was usually up late night due to my work, and he usually went off to sleep way before. I made it a point to wake him up late so that he’d have to hurry to catch the bus. Could spare no more than a min or two for a shower. In other words, I made it impossible for him to fucking jerk off. No release. By mid-week, the blue balls got so bad that he could barely walk.

I hinted many times that I knew he had spied on me. All I wanted was a confession and an apology. He never budged. So a day before his mother came back, I called him out on it and said that I knew what he had done. He finally accepted that he had been snooping. He also said that he had a RECORDING!! The little fuck had the gall to blackmail me. He said he’d give it back if I gave him a blowjob. I told him he’s making a big mistake threatening me. I didn’t speak of it again.

The next day, I had called his mother over for dinner. She had a late-evening flight. It was a Sunday and I allowed Alex to sleep-in. It was during the monsoon and I told him that his clothes hadn’t dried. Except for one t-shirt and a pair of pants. I fiddled with the zipper to break it. And no underwear. I had dressed very conservatively.

He didn’t make much of it and he sat down for dinner. His mother was seated opposite to him, her back to the kitchen. This a rough diagram of what it was like. After they were seated, I told them that I was just going to freshen up a bit. I went into the bedroom but didn’t close the door. The window that was present is quite reflective. I knew Alex could see me. I had to change outfits and without going into detail, let me just say that I put on the sexiest fucking striptease he’d ever seen.

He had to maintain a straight face while still talking to his mom at the table. And with no zipper, his dick was out, whether he wanted it or not. Not that I had seen it. It was under the table.

I came back and during dinner, I had to frequently go to the kitchen to get items and I’d bend over. A lot. I made sure he was rock fucking hard and throbbing under the table. While I was reheating something, he texted me, saying he was sorry and begged me to stop. I asked why, saying this was what he wanted. So, get this: after a week of no release, he was so close that he’d blow the second he touched his dick. He couldn’t even put it away. He was trapped.

I finally had him and asked for the recording. He said it was on his phone. When I stopped at the table, I took his phone to confirm. All the while, I was conversing with the mother, who had no idea what was happening. The footage was recorded in poor light, digital zoom to the max, and barely viewable.

I got what I wanted, and it was time for the killing blow. For dessert, I was heating caramel on the stove and while doing so, I had a popsicle. And I worked it like it was a fucking cock, all while looking straight at him. He blew. All over the floor below the table. I guess he cupped it with his hand to prevent too much of a mess.

After dessert, I told his mom that Alex had to still pack up and that he’d be over soon. After his mom left, I sat down at the table and asked him what he usually fantasized about while jerking off. All the cards were on the table and I asked him that point-blank. I said I wanted to hear it. He was intimidated and started softly telling me. I said LOUDER. And made him say it. Once he was done, I told him that I recorded it. Then I said I knew he probably made a backup of the video and asked him to give it to me. I warned him that if he ever played games or threatened me, I’d take the recording to his mom.

He cleaned up and went home.

EDIT: Bonus Pic

EDIT 2 : Another bonus pic