[F] Flirting with my daughter’s boyfriend – update 30

A lot has happened in the last couple of weeks and I have been waiting for the right moment to post about it all. But there has been no right moment, so here are the major updates.

Since the last time that I posted, I have been extremely horny with anticipation and I think it shows in my behavior around him. The first time that he visited after that night when he almost made a move on me, I was possibly the horniest I’ve ever been. So, sleeping was out of question. I was awake in the middle of the night, knowing that he will either text or knock on my door. And he did. I sprang from the bed to open the door. I thought he’d wait for me to say something, but he slid in and softly closed the door behind him. I was breathing heavily. I was in a shirt and shorts, not too attractive but not very shabby either. He placed his hand on my neck, and without grabbing it, kept pushing me back till I reached the bed, and then said “Is this spontaneous enough?”. He pushed me on the bed and got on top of me. He held my face and pushed it up and kissed and licked my neck, which sent shivers down my spine. I was too stunned to react but I was enjoying it all. He then started making out with me, his hands were roaming on my thighs, boobs, waist, and butt. He was wild. And I was enjoying every moment.

But in my mind, there was a nagging question “Is it worth the risk?”, and I kept repeating that question to myself. He had his hands on my boobs and he was licking my cleavage when I had that question for the first time and then it just did not go away. I did not want to stop him though. I was enjoying every bit of it. So, when he unbuttoned my shirt and started sucking on my nipples, although my mind was asking me if it was worth the risk, my body was happily letting itself be used. I was moaning and running my hands through his hair. But my expressions must have shown some of what was going in my mind, because when he got his face out of my cleavage and looked at me, he asked “what’s wrong?” and I replied “Is it worth the risk?”. He was very confused but he also was too lost in the moment. He went back to licking and biting my nipples and I went back to moaning and overthinking.

He then tried to slide his hand in my panties and I simply could not open my legs. That’s when he stopped and asked me what was wrong. I told him how I stand to lose so much if he ever tells anyone about this and how none of this fun is worth the risk. He got a little annoyed but soon composed himself. He looked at me, very straight in the eye and said “I’m not going to make you regret this. This stays between us” but I am sure I was still very worried, because he said, reluctantly, “If you are worried about ___ finding out, then, …, then, you just have to trust me that the kind of things that we do and talk about make this look pale in comparison”. One part of me was relieved but the other was more concerned and I asked “What have you gotten her into?” and he, almost offended, but somehow still with pride, said “Miss, she has gotten me into as many things as I have gotten her into”.
I sighed, not knowing how to respond. But I told him that I needed more time to think it through. He was surprisingly okay with it, and said “Look, you take as much time as you want, and let me know if I can help. I can understand that from your perspective, this is complicated”. I asked him “Is it not complicated for you?” and he laughed and said “Not as much”. Since then, he as kept true to his word and has waited for my signal.

Fast forward a week or so.

It was his birthday a couple of days back and although I did not go to the party (I did not want to be the only old person in there), last night, finding a moment of privacy after dinner, I whispered in his ear, “Birthday gift tonight”.

I put one of the few lingerie that I have, and waited. Around 3 am, I heard a knock. I pulled him in. He was ready to jump on me, looking at me in that lingerie, but I stopped him. We were both still standing, and I rubbed my body against his, and whispered in his ear “I don’t know if I want to fuck you, but I want to gift you this”, and got on my knees. He was so hard just hearing those words. I played with his cock, teasing him by touching it over his boxers. I slowly pulled them down and finally held his cock in my hand. I was shivering. It was very warm. I gave out a moan just holding it in my hand. It was somewhat dark, so I could not see all the details but I liked what I saw. I started stroking it with my hand but avoided eye contact with him. I could see how eager he was to get what I had promised. I wanted him in my mouth too, so although I had planned to tease him some more, I could not. I started licking it first, from the tip and along the shaft. My mouth felt very dry, possibly from the heavy breathing and I remember licking my lips often. And after licking my lips, I’d rub them against his cock. I liked how I was teasing him. And I liked how desperate he was to put it in my mouth. Almost subconsciously, I looked up and made eye contact with him, which drove him crazy.

He held my hair and in one smooth motion, pushed his cock as far as he could. I could not take him all the way and had to cough and get away for a breath. I said “easy”, which didn’t have much of an effect on him. He tried it again, but gentler. It went farther this time, but not all the way. I was enjoying the fact that he was too big for my mouth. I made it up by licking his cock in circles around the tip. He was going crazy. When he could not take the teasing anymore, he said “come here you” and with his hands still in my hair, pulled me to the edge of the bed. I was in no mood to tease either. I started stroking his cock with my mouth. Every stroke, he tried to push it just a little further than what I could take. I liked how he was being rough but considerate. I placed my hands beside myself, indicating that he can take the lead if he wanted. And he did. I stopped moving my mouth and he did all the moving thereafter. It took all of my effort to not gag too badly, but I managed. He asked me if he could cum in my mouth and I said “Maybe on your next birthday”. He said “Bitch” but pulled out and let me stroke him instead. I only had to stroke him with my hand a few times and his stuff was all over my hands. I looked at him and got up and sat on the bed.

He sat beside me and said “That’s not it, right?” and I replied “I’m sorry, I am really unsure about any of this but I can convince myself that this is a good birthday gift. I will let you know if that changes”. Then he got a little emotional and thanked me a lot. Right before he left, he said “You know I’m going to fuck you like a little….. you’ll see”.

Since then, he has again been respectful of the boundaries. And I have been feeling guilty and ecstatic and horny in phases. Right now, writing this, I am in the horny phase.

Source: reddit.com/r/gonewildstories/comments/ybpglh/f_flirting_with_my_daughters_boyfriend_update_30