One night I came into Fred's room in my dressing gown, while he was lying in bed. I knew I fancied him and was fuelled by my experience at prep school (Story 1), so I wasn't too nervous when I asked him to play a game where I would 'test' him. My cover, for fear of him telling other people about me was that it was a joke and I would see how far I could run my hand up his leg without him flinching. At first Freddie didn't sound like he wanted to but I continued to laugh it off and just went for it. He was lying on his front in some pyjama bottoms, and I started at his ankle and made my way slowly up his thigh, and gently rested on his firm young bum cheek. My dick at this stage had grown and I had a full erection, however my hand rested on Fred's bum a little too long and he became uncomfortable, asking if I was gay etc and pushed my hand off him. I again tried my best to laugh it off, saying it was only a joke.The next night I was in his room again, and over the course of a few days. ’ I smiled even bigger and held my hand directly under his beautiful cock that just happen to be pointing straight out of his body. ‘May I?’ I asked and he looked at me very puzzled. ‘You mean I’m going to have to give hand jobs, too?’ He said worriedly. ‘No,’ I assured him. ‘But this was not supposed to be in my box of oils and now it’s on my hand, you have an erection and I hate wasting anything.’ I paused, looked straight ahead at his cock and smiled. “It would certainly help your stress but I’m not going to wait long for an answer, you know. I would certainly understand if it were too….” He moved his thick cock back into position directly over my hand before I could finish. “awkward for you” I slowly pushed out the last few words of my sentence while wrapping my fingers around his pulsating staff and began to work the oil in, lightly at first but then my grip grew stronger as I came back up his shaft and held my finger and thumb just below the head of his cock. I stopped briefly.
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