Illing Me Softly

I was traveling in another city when I met Sally. She was a waitress at a small 24-hour diner, working the night shift, when I approached her and asked for a coffee.

“Still out this late, mister?”

I nodded.

“I‘ve got some business in town and unfortunately I can’t get a motel room, so I thought I'd leave early and check out the town.”

“Not worth it,” she said curtly, laughing. “You'd better be well rested when you go to your appointment.”

“Well,” I replied, “I don't think the motel room situation has changed much in the last few hours.”

She smiled. “Just come with me,” she said, “I'm almost off work.”

I looked at her for the first time. She was plain but not unattractive, had long wavy red hair and looked quite sexy. She was slim and had a good figure, but it was her small breasts that caught my eye. It wasn‘t until now that I noticed that she wasn’t wearing a bra and that her small, beautifully shaped breasts were showing through her clothes.

My cock seemed to awaken from its hibernation and began to rise in approval and I saw the waitress in a different light. I was undoubtedly more attracted to younger women in their twenties. She was probably at least in her late 30s or even past 40, but that didn‘t make her any less attractive. On the contrary. Suddenly I found it very exciting to go to bed with a more experienced woman. I’d never slept with a woman older than 29, and I began to feel a childlike nervousness, even though I was certainly the more experienced of the two of us.

We soon found ourselves on the subway – on our way to her apartment. We started talking and she told me more about herself. That she had to do this night job because she had separated from her husband. Apparently he had turned out to be a real asshole after the hasty marriage. He hadn‘t beaten her, but he had belittled and humiliated her because he didn’t like her body. Apparently, he felt cheated because he didn‘t like the shape of her breasts and hadn’t had a chance to “test” them before the wedding. As if one could take a “test drive” – or rather a “test ride” – before the wedding.

She had played this undignified game for 20 years before she had had enough and left him.

Meanwhile, my insides had become a roller coaster of emotions. First, I felt sorry for her because she had put up with him for so long and endured his humiliation. On the other hand, her descriptions fueled my hope that she had exactly the kind of breasts I liked so much: small, slightly tubular, with a large nipple at the tip that spanned the entire front of the breast like a cute but hot umbrella. My cock confirmed my hopes with a hot pulsation.

When we finally reached her small apartment – really nothing more than a room with a small kitchenette and a tiny bathroom – I wondered where I was ever going to sleep, if not with her on the small sofa bed, or if she had the same plan as me from the beginning.

We looked at each other, undecided. Then I grabbed my heart and said: “You never intended for me to sleep with you, did you?”

Her eyes no longer held mine at that question. She lowered her eyes sheepishly and managed only a hoarse “Yes”.

She cleared her throat and then it just came out: “I haven‘t had good sex for more than ten years, oh no, I haven’t had sex at all, except for that little hustler who usually only did it with older gentlemen and took care of me out of pure compassion.”

I could feel her fighting back tears now. “I‘m so fucking insecure,” she said, “he’s always made me feel like I'm too ugly, like my tits are ugly. Are they?”

We looked into each other's eyes for a long time before I started undressing her. Very slowly and carefully. First the jacket, then the top that had protected her breasts so well. I slowly took off her shirt, slowly and carefully. I deliberately took my time so as not to suggest any stress. Stress was the last thing she needed right now.

Out of the corner of my eye I realized with satisfaction that I had raised my hopes. However, I continued undeterred and began to unbutton her jeans. I pulled them down to her ankles. Then she gently pulled them off one leg at a time and used her hands to pull the socks off her feet.

Now she was finally completely naked and she looked beautiful to me. For me, everything about her was just right and I suddenly felt very grateful that I was allowed to undress this body.

My heart was pounding like crazy – just like my very first time, which I could barely remember. The tension was almost unbearable.

But I had to be patient, because now it was Sally‘s turn to unwrap today’s ‘gift’.

Sally was hungry and impatient. She didn't wait long for the appetizer, but went straight to the main course. She hurriedly fumbled with the buttons on my pants until she finally found a start. She pulled her pants down to her ankles and then her underpants. She had to be a little more careful because my cock was already almost fully erect in my underwear.

Shortly after that I could feel how much of a hurry she was in. She only pulled my pants down to my knees. She knelt down in front of me, grabbed my cock with one hand and began to lick my glans to her heart's content. She literally “worked” it with her tongue. She began moving my penis back and forth with her hand. She then proceeded to gently but firmly penetrate the small hole at the front end of the glans with the tip of her tongue.

That was wonderful! I felt one pleasurable shiver after another go down my spine. I could also feel how much fun she was having. Every now and then she looked up and smiled.

I closed my eyes and moaned as she licked and sucked harder on my cock. Her hand squeezed harder and she worked my cock even harder, making it even harder.

“I'm going to come soon,” I moaned, whereupon she paused and slowly pulled my stiff cock out of her mouth with a pleasurable smacking sound.

What's next, I thought, but I was about to get an answer to that question – and I liked it.

She straightened up a little more so that my cock was now right at the height of her wonderful little tits that I couldn't have imagined in my wildest dreams. Then she leaned forward and touched my cock with one of her breasts. I thought I was going to explode.

She began to move her breast in circles around my glans and began to moan herself. I immediately joined in the chorus of pleasure.

Then it was her other breast's turn. She started breathing harder and moaning louder. Looking down, I saw that her pussy was completely wet and starting to drip. An orgasm became more and more urgent for me.

After a while it almost felt like a kind of trance. It was a wave of happiness and ecstasy. I wondered if I would ever come, or if I would stay in this ‘just before’ state forever. But then finally – she was wildly throwing her sweet, tender breasts over my cock – this wonderful shudder overwhelmed me.

I came. And how! My cum spread all over her small, fragrant tits.

Exhausted, I sank to the floor and Sally cuddled up to my naked body. As she licked the cum from her breast with her fingers, she took my hand and brought it to her vagina.

“Rub!” she commanded and I began to slowly stroke her clit. She sighed contentedly and surrendered completely to my touch. The arduous but blissful climb to the peak of pleasure began again. At first I worked the pleasure folds of her vagina very gently and slowly, but I steadily increased the pace.

As the speed of my hand on and in her vagina increased, so did her pleasure, which I could tell by her moans and the rapt expression on her face.

Finally she came. Her body jerked violently and she literally screamed out her pleasure.

Then, exhausted, she let herself sink into my arms. She had a satisfied, blissful grin on her lips and she was breathing: “Thank you.”

“No, I have to thank you, Sally. It was wonderful.”