Uni days
I shared a house at uni with one guy and three girls. I became particularly close with one of the girls whose room was on the same floor as mine. She was about 5'9'', average looking, brown hair and thin but with big boobs -- she was probably about a 30DD. I can't remember how it started, but she had what I can only describe as an "ethnic massaging tool" she had picked up in South America on her gap year. We started giving each other massages during the day as it was towards the end of the year and exams and essays were due, so there was a certain amount of stress around.
A key moment must have been when the door got closed. I suppose neither of us wanted our fellow housemates to know, but as soon as the door got shut, it stayed shut, so every time we massaged it was in private. We were also usually in our pyjamas by now as the massages were happening during the evening. This meant thin cotton and no bra for her and no underwear for me -- any erections would be highly visible!
It was suggested (can't remember who by -- probably me!) that we could do a proper massage with some special oil I had been given by an ex. The first time this happened I expected her to be reserved about being topless so offered to leave the room while she got settled, which I did although she said I didn't need to. I came back in and got stuck in, concentrating on her back but letting my hands slide over the side of her boobs. When I finished she put her top back on while I turned my back then she returned the favour. Afterwards we lay on the bed with me still topless.
The next time I didn't leave the room while she took off her top. She took it off with her back to me and when she lay down I got a good view of the nipple of her hanging breast.
I realised that if I let her go second next time she would have to decide whether or not to put her top back on afterwards, with the chance she would stay topless while we chilled. When the time came (maybe a week later) I asked to go first. Once she had finished massaging me and I had done her (with side-boob-touching) I lay down next to her and she stayed topless! She wasn't showing everything and had her arms over them as she lay on her side facing me and we talked.
By this stage it was becoming clear that she really liked me, but the feeling wasn't mutual. I didn't really fancy her and just couldn't see us working as a couple although I really liked her boobs!
There must have been a few more times like this when she lay topless afterwards.
The next time I remember is when after she had done my back I suggested she do my front. This basically involved her sitting astride my hard dick (we had been sitting astride eachother when massaging backs, so this was expected). I don't remember her particularly resting on my dick, but there must have been contact through our thin cotton pyjamas. I then massaged her back then lay down with her. After a couple of minutes I got up the guts to suggest I do her front too ("in a totally non-sexual way"!). She agreed straight away, trying to be cool about it I think! She sat up and unbuttoned her top then lay down. I spent a long time circling her boobs and then lightly ran my hands over them. I repeated this, growing in confidence as she seemed to be having a nice time. I massaged down to her bottoms then stopped.
The next time I made the mistake of kissing her. I kind of expected her to meet me half way when she realised I was going in for the kiss, but she let me go all the way to her, looking reluctant but didn't resist. Things then got sexual between us. Not long after we started having sex on an occasional basis, but I think it was clear to both of us that I was using her. Things really came to an end when I started seeing someone else.
I've always wished I hadn't kissed her, as it would have been amazing to see how naked I could get her in a "non-sexual" way. "Non-sexual" nudity (by that I mean overtly unsexual behaviour whilst naked -- what's going on in my mind is a different matter!) is a massive turn on for me. I reckon it could have gone far with no move being made by either of us, as she was definitely waiting for me to make the first move. If only I had waited!
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