Chapter 30 - The Ultimate Handjob
I met Diana 3 years ago, when she was in her early 30's. She was an ex-student of my bi-friend Jake, before he retired as a high school history teacher. The day we met, she had been staying with Jake, and he had encouraged me to drop by to see what might develop. He intimated that she just might be ready for a three-way. I got to his place mid-morning and was introduced. She was cute as hell and very friendly. In the living room, she sat in a recliner and I was on the couch opposite. As we chatted, she'd shift periodically and give me a good peek up her dress at her underpants (I didn't find out until later that it wasn't inadvertant).
Somehow we got on the subject of sex, and during the conversation I made the observation that I'd never performed oral sex on a woman. She seemed to find that fascinating, and commented that I'd really been missing out. As I got up to leave, she suggested that I come back that evening for dinner. Needless to say, I accepted.....and did return - but not for dinner, as it turned out.
I arrived with wine in hand later that evening, and I remember clearly that she was dressed in a light blue sliky kimono. At her suggestion we adjourned quickly to the bedroom, where Jake removed his clothes, and suggested I do the same, which I did. Diana was propped up on pillows watching with great interest as we undressed. She said that she loved the sight of a man's erect penis. Then Jake had me lay down, and started sucking me off. As I lay there face up, she slid over, leaned down and kissed me, gently at first, then with her entire tongue in my mouth keeping her eye on Herman as he licked up and down on my penis below. God, it was hot! After a few minutes of that, I reached my hand into her robe and started gently massaging her tits as we kissed. They were very nicely shaped, and her nipples became immediately hard. Then I shifted my hand down her stomach to her panties. She was moaning very softly throughout. I slipped my hand under the waistband of her pink cotton Jockey underpants and felt her well-trimmed bush beneath. She untied her sash and let the robe fall. As we continued to French kiss wildly, I slowly inserted my hand inside her underpants and my finger into her well-moistened cunt opening. I absolutely couldn't believe my incredible luck, as I looked into this cute teen-like face of this adorable young girl. I was almost old enough to be her father.
Jake wrapped up my my blow job - I hadn't cum yet, and walked around the bed to remove Diana's panties. She was completely naked now, and absolutely gorgeous. I started furiously finger-fucking her at this point, and she was thrashing around a bit. She then positioned herself on all fours, and Herman entered her from behind with me looking up from below, giving me a bird's eye view of his cock sliding in and out of her pussy.....what an truly erotic sight. I licked her clit for awhile while he was fucking her. She had her first orgasm almost immediately, and cried out and shook all over for 5 or 10 seconds. Then Jake stopped his humping as he pumped his load inside her. After he withdrew, I got her off once more as I licked the semen oozing out of her pussy.
Finally we unclinched, and she laid me back down and said that she had never watched a guy ejaculate up close. She wiped some cum from her bottom, and smeared it on my cock. Then she started jacking me off as she and Jake watched. In less than a minute, I arched my back, as her hand continued to pump, and announced "I'm cumming". Diana cheered as she watched my sperm spurt a good 6 or 8 inches in the air, spurt after spurt. I can't ever remember having an ejaculation quite that intense.
After that, we must have laid there for a good 15 minutes before anyone moved. My God....what a session, and one that was totally unexpected in it's intensity. We met again exactly a year later at Jake's new place, and the action was even better. What a find!