I've had a crush on my straight friend since junior high, but never did anything to let him know. We go to different colleges now, but this past spring break, we went to Florida together, and shared a room. One night he ended up picking up this kinda skanky looking girl, and he asked me if he could have some private time in the room with her. I agreed to sit on the bench across the street from the motel room, and when the light came back on, knew it was okay to come back.
I sat on that bench, staring at the dark window, with a huge boner knowing he was about to have an orgasm. The light came on, and I went back to the room. He let me in, and the room smelled of sex, Ken was shirtless in a pair of gym shorts, and the skank was dressed, lying on his bed watching TV. I grabbed a beer, a laid on my bed, while Ken plopped back down next to her. She put her cheek on his bare chest, and was absently rubbing her fingers across his chest and stomach, toying with his nipple and navel. His nipple rose to the attention, and the sight made me hard.
They started making out, and Ken pulled the comforter up to their waists, his back facing me. He was feeling her tit, and she kept pushing his hand away. I sipped on my beer and watched the show. Ken reached his hand up to hers laying on his waist, and directed it under the covers. A couple of minutes later, he rolled onto his back, lifted his hips off the bed, while he was obviously pulling his shorts down. I could see her hand moving up and down under the covers, as she was obviously jerking him off, with her cheek resting on his left nipple, staring down at his covered crotch.
Ken lifted his right arm over his head, exposing a dark black mass of pit hair, and stretching his smooth skin over his visible ribs. His eyes were closed, his head facing the ceiling, his mouth half open, his nostrils flared. I thought I was going to cum without even touching myself. She turned her head and starting flicking his right nipple with her tongue, and Ken started to lose it. I could see his chest heaving from his heavy breathing, and he turned his head back and forth, as she picked up the pace with her hand job. His head froze facing me, and Ken arched his back. He opened his eyes, stared right into me for a couple of seconds, then his eyes rolled back, he exhaled audibly, and turned his head back to the ceiling. My dick was leaking huge amounts of liquid, having just seen my biggest fantasy have an orgasm feet away from me. The skank stopped, then pulled her hand out, and wiped it first on his chest, then on the comforter. Ken looked down at the wet slick on his chest, then at me with a 'I can't fucking believe that just happened' shit eating grin, then raised his hips under the comforter, and pulled his shorts back up. I just sat there, my knee up to hide my fucking boner. About ten minutes later, she asked Ken if he would walk her back to her motel. Ken hopped out of bed, threw on a shirt and they left.
In seconds, I had the safety lock on the door, Ken's comforter pulled back, and my shorts off. I found the wet spot where he shot, and felt its warmness and stickiness. I pulled it up to my nose, and inhaled it, as I pulled on my dick furiously. I came quickly, and then wiped up my chest with the wet spot of the comforter. I pulled my shorts back up, unlocked the door, tried to put the comforter back about where it was, and got back on my bed. After my woody went down, I went to take a leak, and saw his used condom from earlier in the trash can. I picked it up, and looked at the tip which had a huge load of cum in it, and I started to get hard again. Just then, I heard the door open, so I dropped it back in the can, flushed and went back in the room.
Ken was laughing hard, and it made me laugh too. Then he lifted up his shirt, exposing his nipple to me, and asked if she had left a mark, (she didn't, but I really liked inspecting it close up). Then he was laughing about the look on my face when she was jerking him off, and I told him to never let anyone take a picture of his face during an orgasm, as he looked like someone that was on the verge of barfing, and I made an animated imitation with my mouth open, eyes clenched, and rolling my head around. He laughed, and hit me on the shoulder, then lifted his shirt again, fingering his nipple. He started saying how no girl had ever done that before, and how incredible it felt, and then asked me if I had ever had it done. I shook my head no, told him I had enough with his nipples, and watched the end of the movie. He laid on his bed, and when he felt the huge wet spot with both our cum, he looked at it, muttered 'holy shit, I made a big fucking mess', then tossed the comforter on the floor. When I went to pee before turning in, the condom was gone, assume Ken flushed it when he had gone for a pee.
I laid there, fantasizing about me being the one whacking him off, and me sucking on his perfect nipples until he exploded in my hand. It was my fantasy for months after, and I'm gonna go spew one now, reliving it one more time.