If only I had...

[agaroth]

While waiting for my other posts to be approved by mods, decided to start this thread on all the near misses and what-ifs you've ever encountered. I've had so many that I don't even know where to start... so here's the chance to add a little fiction and imagine what should have happened. Do share yours here!

Ok, first one for the road. There was a time when I used to help out a friend of mine by giving her sister tuition. She was a stunner and had really huge C cup boobs. The worst part is - she doesn't wear a bra when she's at home! How do I know? I usually sit beside her when teaching, and she likes to wear oversized shirts. Then as she's doing her work, she'll like to lean in towards me and adjust the neck of her t-shirt. After awhile, it starts to slip down to one side and I have an excellent down blouse view to the shape of her breasts... How to concentrate on teaching like that??

The thing that drove me crazy was how I could never get a clear view of her nipples though, always having a little bit of the t-shirt covering. I always get neckache from trying to look but pretending not to look at the same time, really silly.

Anyway, we had a good relationship, I was always joking with her, and when she makes mistakes I will playfully poke her sides or squeeze her thighs. Dunno how it evolved, but eventually I always put my arm around her waist while teaching her...

[veri]

Wow , good start , please do continue :)

[agaroth]

Dunno how it evolved, but eventually I always put my arm around her waist while teaching her...

For awhile, that's all it was. Just a friendly poke and tickle to disturb her. Then one day I was tickling her really violently and she was squirming all over the place. I had my hands wrapped around her so she couldn't escape, and in the spur of the moment, I squeezed those huge, braless boobs of hers. I had never touch a girl's boobs before that and it was an instant turn-on. However, I was also feeling very guilty after that heavenly squeeze and released my grip on her.

She was still giggling after the tickling and didn't show any signs of anger or surprise, but just smile and excuse herself to go to the bathroom. She took a while to come back and I was wondering if she had gone to complain to her sister or something and was starting to feel a little nervous. Luckily when she returned, she acted like nothing happened. But for the rest of the session, I didn't dare to touch touch already.

Looking back, I should have pressed the advantage since she didn't resist. Subsequently, I would always stroke her thigh and the underside of her boobs, one time I went as far as to stroke her pussy from outside her shorts, and she instantly pressed her hands on mine to push it away. But she never made any other objections or complained about our physical contact.

Everytime I think back, I can't help but kick myself for being too hum chi to go a little further. If I had discovered this forum back then, I think I won't be so polite to her, hahaha.

Any bros got stories to share?

[alan0338]

Everytime I think back, I can't help but kick myself for being too hum chi to go a little further. If I had discovered this forum back then, I think I won't be so polite to her, hahaha.


bro, u should consider urself lucky for nv doing something crazy :)

[1nottiboy]

Many years ago, when I was 16 and studying overseas, I went to visit my friend at her house. She was not in but her room mate, Yen, was. Yen invited me in and I agreed. After closing the door, Yen went back to her desk to continue doing her revision. Curious, i stood behind her and asked what she was revising. I then noticed that she was braless and I could see her nips. She then said that her neck ached. I was too young and stupid then. Did not catch the hint to give her a massage. After waiting for 15 mins, when my friend had not returned, I decided to go home. Yen walked me to the door, streched her arm across the doorway and asked, "Are you sure you wanna go home?"

And the stupid me said, "YES." Wat a fool!!!