Talk about being in the right place at the right time... A long ago something happened to me that taught me the value of how much a little honest, complimentary praise can mean to a needy woman starved for attention.
When I was 15, I was struggling with math class and my mom arranged for an accountant she knew from work to tutor me in private lessons at his nearby house. He was apparently a very busy man, because sometimes he would show up and sometimes he wouldn't. However, his wife was always home and was always very friendly, kind and courteous. In fact, I was enamored of her... a typical schoolboy crush for an older, very attractive, more sophisticated woman. Even though I had a girlfriend at the time, I'd hang out with her during aborted lesson times anyway because she was so intelligent and captivating, and we had many stimulating discussions on all kinds of topics. Although I knew nothing could ever happen between us, I couldn't get enough of just being around her.
As the school year wore on, I understood that they were expecting their first child, and her husband was around even less frequently than before. One early evening (right after school) I arrived for my scheduled appointment and Shelley answered the door wearing a robe and seemingly distracted. She asked 'He didn't let you know he was going to be out of town for a few days? What a jerk.' She invited me in anyway, and said 'You know I love our conversations, but would you mind just watching TV for a while, I'm right in the middle of something.' I sat in a chair, and she seated herself on the left end of their sofa. I noticed that she was rubbing her chest with a terrycloth washcloth in one hand under her robe. I finally inquired what she was doing, and it was like I'd awakened her from a trance. She explained, 'Oh, I'm really looking forward to breastfeeding our baby, I've extensively researched the beneficial health aspects and intend to nurse well after our child is teething. So my doctor put me on a 'nipple preparation' regimen, and this is just part of my routine.' There was an awkward silence as I felt both uncomfortable and aroused at the same time. She broke the silence by continuing, 'The program started out with me just pulling and stretching my nipples out with my fingers, then using paper towels, and now this final step involves twisting and rubbing them with the roughest texture I could find.' Needless to say, I was no longer interested in watching whatever was on TV; I couldn't take my eyes off her.
Eventually she said, 'You know, I can think of an even better way to toughen these up, if you'd like to help me out. Come over and sit down next to me, don't be such a stranger. We're friends, right?' So I moved just to her right on the couch. In her erudite manner, she admitted to me that her husband was a textbook example of 'that Madonna-Whore Complex thing. We used to have a great love life, but since I became pregnant, he has no sexual interest in me at all. I'm sure he's getting his somewhere else now, though.' With that, she loosened her robe and slipped her arms out through the sleeves, revealing beautiful, although somewhat pendulous breasts, pale blue veins visible beneath her porcelain skin, and dark brown areola at least the diameter of Coke cans.
'What do you think of these?' she asked, cupping her hands under her swollen breasts, jiggling them as if weighing melons at the supermarket, 'I used to have such an athletic build, but now in my sixth month, my titties have gotten so much bigger. Feel how heavy they are...it's OK.' Just seeing them was too much for me, and I hesitated. 'Oh, you're just like my husband, you don't like the way they look either,' she sighed disappointedly.
'No' I managed to croak out through my suddenly dry throat, 'I think you have the most beautiful, sexiest breasts I've ever seen.'
Brightening considerably and flashing a grateful smile that lit up the room, she squealed 'Really? You're so sweet. Would it be too weird if I asked you to help me condition them?'
'Uhhh, I don't know about that,' I stammered, feeling my palms sweating and feeling flushed, 'they look ready for anything already to me.'
Her nipples were as thick as the corks from champagne or wine bottles. 'You don't think they're gross, do you? My husband does.'
I replied again that I sincerely thought they were the most beautiful things I'd ever seen in my life.
'Well, you've certainly made my day,' she murmured, 'c'mere.' She put her right arm around my shoulder, turning me sideways and leaning me back so my head rested cradled inside her left elbow. 'Just suck on my nipples,' she said, 'you can even bite 'em a little...not hard, though.'
I don't know how long I'd been doing this, because it was so calming and peaceful, before she warned 'Oh, don't be alarmed if you taste some liquid in your mouth...it's just colostrum, a kind of pre-milk secretion before the baby is born.' I was so engaged in all this that Shelley noticed I had a raging erection. The next thing I knew, she was fondling it through my pants. 'Oh oh, this can't be very comfortable, let me take it out and make some room for you down there,' she said naughtily, 'here, switch to my left breast, will you? We've got to even this treatment out, plus I can get at you better that way...should I?' I tried to mumble 'uh-huh' now with my mouth on her other turgid nipple, but she cooed 'Ssshhh, just relax...while you're doing that, I'm going to beat you off...you want me to?'
I'll never forget the look she gave me when our eyes met, gazing up into her caring, giving face, nodding 'yes' while still latched onto that unbelievably sexy nipple, making her full breast bounce as I did so.
She undid my pants and scooted them down enough to release my penis. She informed me 'Sex is all about signals, and the brain is the most important erogenous zone of them all,' and proceeded to start slowly, lovingly stroking me. She could tell every time I was close to coming, and would stop and squeeze the tip with her thumb and fingers. My heavy breathing would temporarily subside, and she would start up again, a little faster and more intense each time, then stopping and squeezing again. After a few cycles of this exquisite teasing torture, she mercifully asked, 'Do you want to come yet? When you're ready, just let me know.'
I collapsed back and closed my eyes out of sheer pleasure. Shelley admonished 'Hey, look, concentrate for me.' I stared at her torso slightly bent over and shoulders hunched because of the robe being bunched up in back of her against the couch. Her breasts were bouncing in sympathetic vibration with her wrist and arm movements.
I said 'I think I'm gonna come now,' and she suddenly stopped again, cupping her hand around my balls while pressing down hard at the base with her thumb and forefingers. Time seemed to stand still as she just sat there, stretching my foreskin back down as tight as it would go, but otherwise motionless.
I didn't know what to expect since she had ceased directly stimulating me, and I must have had a weird look on my face, because she looked into my eyes and said 'Ssshhh, don't worry... everything's gonna be all right.' My penis started twitching and convulsing in bursts. I felt the buzz of climax, but looked down and saw she was still just holding me, aiming my swollen red, throbbing head directly at her breast, pointing and touching it to the end of her long, erect nipple, brushing and rubbing the underside of my penis across it, making the nipple bend and then snap back into place, circling the tip around her areola. Suddenly hot streams started erupting out of me. After the first few landed on her chest, she gently milked the last drops out, and rubbed my fluid into her breasts, except for one huge glob that had run down and was dangling precariously from her nipple.
I stammered, 'I didn't think it could happen like that.'
She responded, 'There must be a lot you don't know... Haven't you ever been given a handjob before?'
Not wishing to appear inexperienced, I replied, 'Yeah, but not like that one, anyway.'
She laughingly said, 'Well, you helped me out and I wanted to do you a favor in return.'
A short time later, they moved away, and I heard eventually they'd gotten divorced. I never saw her again, but will always remember the treat of her 'helping hand' that day, and the most intense, prolonged orgasm I'd ever had.