My Older Woman

Roxann was upset. Normally she was very upbeat and vivacious, but instead she seemed down on herself.

“I’m going to turn 50 in a few days” she said softly aloud “and I’m all alone. Nobody likes me and I look awful. Maybe I need liposuction or something?”

Now for the record Roxann, even at 50, could easily pass for a woman in her 30’s, maybe 40 tops. She had been in her “former life” as she put it, an accomplished cabaret singer and dancer, blessed with a beautiful body, and killer legs.

If I had to make a guess, I would say she was about 5’9″ with a perfect 36D-24-36 figure that she kept in great shape with her diet and exercise.

I was roughly half her age, but she was the object of many of my fantasies and desires to make love to an older woman, not that I felt I had any realistic chance to fulfill them with my co-worker.

As much as I respectfully tried to reassure her about her looks, she just politely shrugged me off.

That night, I realized I had a gift certificate from a florist that would soon expire, so I decided to send Roxann the best birthday bouquet they offered along with note asking her to “be my birthday girl”.

A few days later on an afternoon off, my phone rang. It was Roxann. In a very soft voice she asked, “Are you independently wealthy, Johnny?” Before I could answer she added, “You must be in order to afford such lovely flowers for me.”

I laughed and told her she was worth it and that I felt bad they she was not looking forward to her birthday. I decided to get bold and tell her that even at age 50, she looked incredible.

“Women half your age would kill to look half as good as you do, Roxann. Your body is amazing and I don’t want to hear you even mention the word liposuction!”

I stopped short of telling her the only suction she needed was from the lips of an eager and willing young lover like me but I didn’t want to overplay my hand.

Roxann was flattered but brought up not only our age difference but the fact we worked together as two reasons not to take this conversation any farther.

To my disappointment, nothing much came of this other than some innocent smiles and playful flirting but with the holidays approaching, I decided to go all in. This time Roxann would be getting some sexy lingerie as a present.

I picked out the hottest bra, panties, stockings and garter set I could find and had it sent to Roxann, but I was disappointed to not get a call from her a few days later when I was sure she must have gotten it.

Luckily, the company holiday party had arrived and I was certain to see her there.

Roxann looked great as usual at the party, dressed in her typical classy if conservative way.

I said hello to her but our conversation was very brief and there was no mention of my gift. But just before she slipped away, she asked me if I would come and find her when the party broke up and walk her to her car since she had parked a little farther away than usual.

I told Roxann I would and she leaned in and whispered, “this way I can also show you your present, Johnny.”

My heart and mind were racing the rest of the night, dying to know exactly what she meant.

As the party died down, I grabbed my coat and went to find Roxann but I could not locate her anywhere.

Suddenly, she burst out of the ladies room and took me by the wrist, leading me in a hurry to the elevator.

“Let’s go, Johnny…” She ordered as we quickly snuck into the empty car before anyone else could enter.

The door closed and Roxann looked at me with a wicked smile and asked, “Are you ready to see your present?”

Before I could utter a sound, Roxann whipped open her long coat and revealed the lingerie set and nothing else underneath.

“What do you think, Johnny?” She asked, as if the site of the sexy bra and panties accented by the stockings and garter on her spectacular body needed my approval, “do you like your present?”

I answered in the affirmative by pulling her tight to me and immediately began kissing her neck and caressing that amazing figure, but Roxann pushed me away gently and giggled as she told me to wait until we got to her car.

She closed her coat just as the elevator door opened and we went arm and arm into the chilly night. I couldn’t resist stopping a couple of times to share a deep kiss with this sexy woman who was enjoying every second of attention.

We reached Roxann’s sports car and she turned on the engine. My engine was already humming and our foreplay began.

After a few minutes of play, Roxann pulled away from me and we began the drive to her place.

We raced along the highway and she made sure to reach over and keep my cock nice and hard with her free hand, fluffing me for what was to come.

I returned the favor by gently playing with her pussy both over and under the silk panties, getting Roxann nice and wet.

When we got to her cozy home in the hills, she suggested we jump in her jacuzzi. I completely agreed and escorted her out on the deck.

Roxann got the hot tub going and with my eager help quickly wiggled out of her sexy underwear. I helped her into the steamy water and disrobed.

My cock was at full attention despite the cold air and dipping into the tub gave it an extra boost. Roxann wrapped her sexy body tightly around me and I entered her.

“Fuck me, Johnny, fuck me, Johnny!” Roxann commanded again and again.

I obeyed and kept pounding her pussy for all I was worth.

We went at it for a good 20 minutes, switching positions a few times to maintain my composure and my throbbing erection.

Roxann could sense I was ready to explode and let me pull out.

“Cum for me, Johnny baby” screamed Roxann “shoot it on my fucking face!”

I released and released, the spurts of thick, creamy hot cum hitting the target as ordered.

“You are amazing, Roxann” I exclaimed with each spurt “you are so sexy–I love fucking you.”

I kissed her and licked some of my cum off of her face.

“You are such a gentleman, Johnny.” She said. “Now lets go inside to my warm bed and continue our love-making.”

We scurried inside and went at it for hours. Despite being half her age, I could barely keep up with Roxann and her insatiable sexual appetite.

“Thank you for the present, Johnny.” Roxann said while catching he breath in between rounds of our hot sex.

“Thank you for mine, Roxann.” I said and went back to pleasing my older woman.