Still get a thrill thinking about it, though this happened five years ago now.
It was 6:30 on a Sunday morning and I'd woken up as horny as hell. Mornings are my favorite time for sex, has been for as long as I can remember. This particular morning I was alone though, didn't 'get lucky' the night before. Had an 8:00am breakfast date with an old friend which still gave me plenty of time for a good jack-off session and a shower before she arrived.
Put on my robe, got a cup of coffee, grabbed a t-shirt from the hamper in the bathroom and the lube from the medicine cabinet. Sat down at the computer jumped back and forth between stories and pics sipping coffee, it's the stories that really get me going, voyeur and exhibitionism especially, watching and being watched while having sex. Threesomes too, FFM and MMF, done the former a number of times and look forward to the latter sometime with the right people.
Checked the clock, it was almost 7:00am, and decided I'd better get on with it before time ran out so I filled my hand with lube and started slowly stroking. My cock went from that half hard stage to rock solid with about ten up and down motions. My office is situated off the deck near the driveway and parking area, and my desk is in a corner so my back is to the slider opening onto the deck. Well I was really getting into it remembering previous sexual encounters.
I was getting close and stood up with the t-shirt in my hand ready to catch the cum when I noticed Rachel standing at the slider laughing quietly. I quickly held the t-shirt in front of me and tried to hide what I was doing as she walked in still smiling, shaking her head from side to side and doing that 'tisk, tisk, tisk' thing with her tongue. She looked me in the eyes and said, 'I felt the need this morning too, had three very enjoyable orgasms in the shower before coming over here. Those hand held shower massagers are marvellous.'
'Sorry about this Rachel I wasn't expecting you for an hour you know.' 'Charlie, daylight savings time starts today, you forgot I guess, huh.' 'Shit, I did, what a dip shit I am.' 'Give me ten minutes to shower and I'll be ready to go.' 'What? You're going to finish what you started in the shower aren't you?'
'Yeah, probably. Got to get rid of this boner somehow.' 'Charlie, finish here while I watch. It'll give me something to think about next time I play in the shower.'
Well that's all the encouragement it took. I re-lubed my hand and started jacking off again while she sat in a chair watching me. God damn, what a rush. We'd never gone further than talking about sex, and our sexual experiences, with one another. Both of us worried about sex interfering with a friendship I guess. But here I was jerking off not three feet away from her. She looked at me intently and said. 'I've never watched a guy jack off before, had guys pull out of me at the last minute and cum on my belly or tits, or on my ass, but never a start to finish jack off session. Cool!'
I looked her in the eye and said softly, 'Show me your boobs, Rachel.' as I rubbed the swollen head of my cock. She pulled her sweater and t-shirt over her head together in one fell swoop revealing much larger breasts than I'd imagined with probably the largest nipples I'd ever seen in real life. She cupped them in her hands and teased the nipples with her thumbs making them stand out even more erect.
'Wanna come on my tits Charlie?', she asked in a sexy voice and I moved in closer to stand directly in front of her, my cock just inches from her face. She then laughed softly, moved her head back and cupping her tits held them up just under my dick staring at me intently in the eyes.
As I felt my orgasm start I moaned, 'Oh shit, here it comes', and slowed the movement of my hand and pointed my cock down at her boobs. Her eyes dropped immediately directed at the end of my dick as she pushed her boobs up closer. After three or four more slow, full length strokes all the way out over the glans and back down the shaft I gripped the shaft at the base tightly and spurted three or four times before resuming the slow stroking once again milking out the last few drops. I stood there rubbing my softening cock on her breasts spreading my goo across them from nipple to nipple.
She looked at me and simply said, 'Thanks. Here I am 35 years old and I've never seen that before except in porn movies. The look on your face as you started to cum was beautiful.' 'No Rachel, thank you', I replied, 'fifteen minutes ago I was sitting down to a solo jack off session, but instead.... what a treat!' I stepped back, bent down and kissed her lightly on the lips and said, 'You owe me one now, you know.' She laughed and said, 'Yes, I guess I do.'
'You going to shower now, Charlie?' she asked. I said yes and she stood and began removing the rest of her clothes saying, 'Mind if I join you. I think I need another one too,' as she rubbed the sticky wetness on her breasts around with her hand.